Exploring Chicago, IL
Time needed in this city: A long weekend (3 nights)
Note: This post has been updated on May 30, 2024.
Chicago is one of those cities that gets a horrible rap, and it might be somewhat warranted, but not entirely. The city is full of incredible restaurants and plenty of things to see and do, no matter what time of year.
The below information is a complete guide of the best places to stay, the top rated places to dine and drink, and all there is to see and do. We’ve also included transportation tips, as well as a summary of the history of this energetic city!
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Where to Stay
The Viceroy is a swanky boutique hotel right in the heart of the Gold Coast, in a 120 year-old building! The lobby boasts larger-than-life art installations welcoming you to the lobby, there’s a seasonal rooftop pool with skyline views, and most of the rooms have views of Lake Michigan. Oh yeah, and it’s dog-friendly, too!
W Lakeshore Chicago
Never to disappoint, this is easily creeping up in my personal W Hotel rankings to being one of my top 3 favorite W Hotel properties to stay at. From the incredibly friendly staff, to the swank, no-bad-view rooms; as well as the overall high-energy level of the hotel, you would never expect anything less.... unless... you have a view like the one at the top of this post.
Other Recommended Hotels
Where to Dine & Drink
2-d Restaurant
Dine in a cartoon! They serve mochi donuts and fried chicken.
88 Marketplace
A giant eat-in Asian marketplace
Alinea
Chef Grant Achatz draws foodies with New American tasting menus featuring highly creative plates.
Alla Vita
Traditional Italian specialties plated in a stylish, elegant restaurant with a whimsical vibe.
Andros Taverna
Chef Doug Psaltis is the “P” in RPM and this is his first solo project. The restaurant serves seasonal Greek specialties and cocktails, served in a contemporary space with a patio.
Armitage Alehouse
Upscale operation with a lavish old-world-pub theme serving hearty dinners, plus weekend breakfasts.
Au Cheval
Diner with an open kitchen using ingredients ranging from bologna to foie gras.
Bellevue
An elevated restaurant and bustling first floor bar and patio offer a menu of timeless classics and fresh takes, this is the place for sophisticated socializing.
TIP: Go for a glass of wine and an appetizer and if it’s great weather, ask to sit on the patio.
Bittersweet Pastry Shop
Quaint bakery/cafe offering specialty cakes, cookies & breads, plus sweet & savory pastries.
Bocadillo Market
Chef James Martin was inspired by Spanish techniques and highlights similarities between Spanish dishes—particularly those brought over by the Moors of North Africa—and his Southern heritage.
Cherry Circle Room
Modern operation inside Chicago Athletic Hotel offering seasonal house cocktails & a refined menu.
Chicago Cut
One of the newer fine-dining places in Chicago, this steakhouse offers an incredible menu of options, as well as a beautiful dining room that overlooks the river.
Cindy’s Rooftop
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
Esmé
Tasting menu with artisanal creations.
Ever
Luxe establishment offering a fine-dining tasting menu created by an accomplished chef.
Galit
Chef-driven Middle Eastern eatery with regular & sharing menus & creative cocktails in hip digs.
Girl and the Goat
Hot spot where Stephanie Izard serves up innovative small plates from a dramatic open kitchen.
Goddess and the Baker
All-day cafe with baked goods plus breakfast items and lunch, salads, sandwiches. Excellent for gluten-free!
J.P. Graziano Grocery
Long-running Italian market & sandwich shop offering subs & specialty food items since 1937.
Lost Larson
Bakery-cafe serving bread, pastries, sandwiches & cocktails in a casual space with a retro vibe.
Lula Cafe
Inventive, market-driven food in a casual, funky space that hosts an especially popular brunch.
Momotaro
Japanese cuisine.
Obelix
Authentic French cuisine.
Original Rainbow Cone
Has been serving ice cream for over 80 years!
Osteria Langhe
Italian joint serving seasonal Piemontese fare in casual digs with bare woods tables & a rustic bar.
Quartino
This place is old school Chicago-style Italian. As with most of the other restaurants in Chicago, it has it's own exclusive gluten-free menu with quinoa-based spaghetti, as well as the THE BEST risotto I've ever had. I recommend the asparagus risotto on the gluten-free menu.
Rose Mary
Italian-Croatian cuisine is served in an industrial-chic restaurant with a bar.
Shawn Michelle’s Homemade Ice Cream
Petite, understated spot dishing up signature ice cream & sundaes, plus brownies.
Smyth and the Loyalist
Rustic-chic venue offering tasting menus of inventive, high-end New American fare & wine pairings.
Superdawg Drive-in
It’s been open since the 1940s and is everything you would expect!
Tavern on Rush
Bill and Giuliana Rancic dine here and it's understandable as to why. Another Chicago-style restaurant has hit the mark, in terms of great food and great atmosphere. Settled in the middle of all the posh shopping, it's a perfect lunch spot. Their gluten-free pizzas are amazing!
Time Out Market
50,000-sq ft. industrial hub for chef-driven eats and cocktails with communal seats and a rooftop deck.
Tzuco
Upscale, stylish spot for regional Mexican cuisine with craft cocktails and a pastry chef
Speakeasies
Bordel
Milk Room
Room 13
To get in, you can either apply for membership for a yearly fee or earn an invite by staying at the hotel.
The Alderman
The Drifter
The Office
Violet Hour
You would never know it's there because the external façade is a wooden barricade that has been covered by (rotating) graffiti. Once inside, you walk up a nondescript hallway and into what can only be likened as a swank speakeasy. No cell phones are allowed, and you can only be seated once seats are available for your entire party. The music is hauntingly beautiful, giving you a complete experience of being swept into another era, or even world. It's, by far, the most amazing lounge I've ever been to.
Things to See & Do
There are so many things to see & do in Chicago that not only can it be overwhelming, it can also become costly! For the most economical way to gain access to almost all of what is listed below, consider purchasing the City Pass.
Historical Exploration
Driehaus Museum
The Richard H. Driehaus Museum is housed within the historic Samuel M. Nickerson House, the 1883 residence of a wealthy Chicago banker. Although the mansion has been restored, the Driehaus Museum does not re-create the Nickerson period but rather, broadly interprets and displays the prevailing design, architecture, and decorating tastes of Gilded Age America and the art nouveau era in permanent and special exhibitions.
The interiors are teeming with marble, onyx, carved exotic and domestic woods, glazed tiles, and stained glass. On display are original furnishings from the Nickerson era along with American and European decorative arts of the late 19th and early 20th centuries, including art nouveau furnishings and a number of works by Louis Comfort Tiffany. The museum is named after its founder, the Chicago businessman, philanthropist, and art collector Richard H. Driehaus. The artworks on display in the museum are selections from the private Driehaus Collection of Fine and Decorative Arts.
Ernest Hemingway Birthplace Museum
Hemingway was born in Oak Park, Illinois, on July 21, 1899, in a home built by Hemingway's maternal grandparents, Caroline and Ernest Hall. Hemingway was the second child and first son of Dr. Clarence and Grace Hemingway.
In 1905, the house was sold out of the Hemingway family and was subsequently renovated and converted into a multi-family residence.
In December 1992, the house was purchased by the Ernest Hemingway Foundation of Oak Park. The foundation oversaw a major restoration project, using photographs and descriptions of the house, to return it to its original condition. Since 2001, the building has been maintained as a Hemingway museum, with the foundation offering guided tours of the house.
Frank Lloyd Wright Home and Studio
First built in 1889 and added to over the years, Frank Lloyd Wright’s home and studio is furnished with original Wright-designed furniture and textiles. It has been restored by the Frank Lloyd Wright Preservation Trust to its appearance in 1909 - the last year Wright lived there with his family. Here, Wright worked on his career and aesthetic in becoming one of the most influential architects of the 20th century.
The property was listed on the National Register of Historic Places in 1972, declared a National Historic Landmark four years later, and contributes to the Frank Lloyd Wright–Prairie School of Architecture Historic District containing a number of his projects and related work.
Gangsters and Ghosts Tour
With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
Robie House
The Frederick C. Robie House is a U.S. National Historic Landmark now on the campus of the University of Chicago, in the South Side neighborhood of Hyde Park.
Built between 1909 and 1910, the building was designed as a single family home by architect Frank Lloyd Wright and is considered perhaps the finest example of Prairie School - the first architectural style considered uniquely American.
Robie House was designated a National Historic Landmark on November 27, 1963 and was on the first National Register of Historic Places list as of October 15, 1966. The house, as well as a selection of seven other properties by Wright, was inscribed on the World Heritage List under the title, "The 20th-Century Architecture of Frank Lloyd Wright", in July 2019.
The Rookery
Designed by famous architectural partners, Burnham and Root, the picturesque Rookery was originally completed in 1888. Adding to its impressive stature, Frank Lloyd Wright redesigned the stunning two-story, sky lit lobby in 1905. Meticulously renovated and maintained, The Rookery stands as one of the most highly recognized addresses in all of Chicago.
NOTE: You can enter the lobby and take a look around and also visit the Frank Lloyd Wright Foundation for unique gifts and tour tickets.
The Arts & Sciences
Adler Planetarium
The Adler Planetarium is a public museum (it was the first planetarium in the United States), dedicated to astronomy and astrophysics. It was founded in 1930 by local businessman Max Adler and declared a National Historic Landmark in 1987.
The Adler has three theaters, space science exhibitions, including the Gemini 12 space capsule, and a collection of antique scientific instruments and print materials. In addition, the Adler Planetarium hosts the Doane Observatory, a research-active public observatory.
Art Institute of Chicago
Founded in 1879, the AIC is one of the oldest and largest art museums in the United States. It’s internationally recognized for its curatorial efforts and popularity among visitors, its collection, stewarded by 11 curatorial departments, is encyclopedic, and includes works such as Georges Seurat's A Sunday on La Grande Jatte, Pablo Picasso's The Old Guitarist, Edward Hopper's Nighthawks, and Grant Wood's American Gothic. Its permanent collection of nearly 300,000 works of art is augmented by more than 30 special exhibitions, mounted yearly, that illuminate aspects of the collection and present curatorial and scientific research.
The growth of the collection has warranted several additions to the museum's 1893 building, which was constructed for the World's Columbian Exposition. The most recent expansion, the Modern Wing, designed by Renzo Piano, opened in 2009 and increased the museum's footprint to nearly one million square feet, making it the second largest art museum in the United States.
If Ferris Bueller can stop here, so can you.
Chicago Theatre
Built in 1921, the Chicago Theatre was the flagship for the Balaban and Katz (B&K) group of theaters run by A. J. Balaban, his brother Barney Balaban, and partner Sam Katz. Along with the other B&K theaters, from 1925 to 1945, the Chicago Theatre was a dominant movie theater enterprise. Currently, Madison Square Garden, Inc. owns and operates the Chicago Theatre as a 3600 seat performing arts venue for stage plays, magic shows, comedy, speeches, sporting events and popular music concerts.
The building was added to the National Register of Historic Places on June 6, 1979, and was listed as a Chicago Landmark on January 28, 1983. The distinctive Chicago Theatre marquee, "an unofficial emblem of the city", appears frequently in film, television, artwork, and photography.
Museum of Contemporary Art
Established in 1967, this museum is one of the world's largest contemporary art venues. The museum's collection is composed of thousands of objects of Post-World War II visual art and is run gallery-style with individually curated exhibitions throughout the year.
The museum has hosted several notable debut exhibitions, including: Frida Kahlo's first U.S. exhibition and Jeff Koons' first solo museum exhibition. Koons later presented an exhibit at the museum that broke the museum's attendance record. The current record for the most attended exhibition is the 2017 exhibition of Takashi Murakami work.
The museum’s collection includes Jasper Johns, Andy Warhol, Cindy Sherman, Kara Walker, and Alexander Calder. It also contains historical samples of 1940s–1970s late surrealism, pop art, minimalism, and conceptual art; notable holdings 1980s postmodernism; as well as contemporary painting, sculpture, photography, video, installation, and related media. It also presents dance, theater, music, and multidisciplinary arts.
OUR TAKE: If you’re into politically-charged art, then this is your place. Otherwise, we found it to be lackluster and wish we would have gone to the Chicago Art Institute instead.
Museum of Illusions
Per their description, “The Museum of Illusions Chicago is like no place you’ve been before. We are a one-of-a-kind edutainment destination where you can immerse yourself in in the wonderful world of illusions! Guests will enjoy more than 60 visual and educational exhibits featuring holograms, stereograms, optical illusions, and immersive rooms that are designed to tease the senses and trick the mind.”
Museum of Science and Industry
The Museum of Science and Industry (MSI) is a science museum located in Jackson Park, in the Hyde Park neighborhood, between Lake Michigan and The University of Chicago.
It is housed in the Palace of Fine Arts from the 1893 World's Columbian Exposition. Initially endowed by Julius Rosenwald, the Sears, Roebuck and Company president and philanthropist, it was supported by the Commercial Club of Chicago and opened in 1933 during the Century of Progress Exposition.
Among the museum's exhibits are a full-size replica coal mine, the German submarine U-505 captured during World War II, a 3,500-square-foot model railroad, the command module of Apollo 8, and the first diesel-powered streamlined stainless-steel passenger train (Pioneer Zephyr).
Music Box Theatre
The Music Box opened on August 22, 1929 as a single screen theater with a seating capacity of 750 with the opening night film being Mother’s Boy. In 1931, the Music Box was one of several theaters bombed during an ongoing dispute between the Allied Independent Theaters' Association and the Motion Picture Operators' Union as the theater was employing non-union projectionists. Between 1977 and 1983, the Music Box was used sporadically for Spanish language films, pornographic films, and Arabic language films. The theater was shuttered briefly until 1983 when Robert Chaney, Christopher Carlo, and Stan Hightower formed the Music Box Theatre Corporation and restored and reopened the theater with a format of double feature revival and repertory films. Eventually, foreign films and independent and cult films were added to the roster and repertory screenings were moved to weekend matinee and midnight time slots.
In 1991, a 100-seat theater was built in an existing storefront, adjacent to the lobby, opening to the public on July 3rd of that year. "Theatre 2" was remodeled in 2013 to accommodate new digital projection and audio systems, as well as a larger screen. Theatre acoustics were improved, replacement seats were installed, and some rows of seats were removed leaving it with a seating capacity of 75. A bar and lounge were added in 2015, in the storefront directly north of the original building. The lower portion of the marquee was replaced in 2018, it was designed to replicate the original.
Second City
The Second City is an improv comedy enterprise. It’s the oldest improvisational theater troupe to be continuously based in Chicago, with training programs and live theaters in Toronto and Los Angeles. Opened on December 16, 1959, it has become one of the most influential and prolific comedy theaters in the English-speaking world.
The Second City has produced television programs in both Canada and the United States, including SCTV, Second City Presents, and Next Comedy Legend. Since its debut, The Second City has been a starting point for many comedians, award-winning actors, directors, and others in show business, including Del Close, Alan Alda, Alan Arkin, Harold Ramis, Bill Murray, Gilda Radner, John Candy, John Belushi, Dan Aykroyd, Eugene Levy, Catherine O'Hara, Dave Thomas, Chris Farley, Tim Meadows, Colin Mochrie, Ryan Stiles, Mike Myers, Nia Vardalos, Steve Carell, Jordan Peele, Tina Fey, Amy Poehler, Stephen Colbert, Cecily Strong, Mae Martin, and Aidy Bryant.
Unique Experiences
Chicago Architecture River Cruise
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Wrigley Building and the John Hancock Building.
Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
Discover all three branches of the Chicago River with your guide.
Enjoy the best vantage point to admire Chicago's skyline and architecture.
See more than 40 buildings, like the Wrigley Building and Willis Tower.
Discover the events that shaped the architectural history of Chicago.
NOTE: This tour comes highly recommended by locals as well. It’s suggested it be the top thing you do in the city!
Chicago Magic Lounge
Per their description, “Step inside and leave the ordinary behind as you enter through our secret laundry entrance into our luxurious retro-inspired "speakeasy." Indulge in handcrafted cocktails and savor delectable small plates while enjoying awe-inspiring acts performed by the finest magicians in the industry. It's an experience like no other—a remarkable opportunity to witness the art of magic up close and personal.”
Chicago Prohibition Tour
Per their description, “Get a closer look into how alcohol flowed through the streets of Chicago! From the “down and dirty” gangster hangouts, to the “jackets required” establishments for Chicago’s elite, learn what it took for all Chicagoans to get their booze! Follow your guide as they walk you through three iconic Chicago staples where everyone from Chicago’s most notorious gangsters to our most respected members of high society became ‘Scofflaws’.”
Cubs game at Wrigley Field
The Cubs began in 1870 as the Chicago White Stockings, playing their home games at West Side Grounds. Six years later, they joined the National League (NL) as a charter member. In the runup to their NL debut, owner William Hulbert signed various star players, such as pitcher Albert Spalding and infielders Ross Barnes, Deacon White, and Adrian "Cap" Anson. The White Stockings quickly established themselves as one of the new league's top teams.
After back-to-back pennants in 1880 and 1881, Hulbert died and Spalding, who had retired from playing to start Spalding sporting goods, assumed ownership of the club. The White Stockings, with Anson acting as player-manager, captured their third consecutive pennant in 1882, and Anson established himself as the game's first true superstar. In 1885 and 1886, after winning NL pennants, the White Stockings met the champions of the short-lived American Association in that era's version of a World Series.
In 1890, they became known as the “Chicago Colts”. In 1902, Spalding, who by this time had revamped the roster to boast what would soon be one of the best teams of the early century, sold the club to Jim Hart. The franchise was nicknamed “the Cubs” by the Chicago Daily News in 1902 - it officially took the name five years later.
From 1905 - 1912, the Cubs won four pennants and two World Series titles over a five-year span. They would not win another World Series until 2016.
About Wrigley Field
It first opened in 1914 as Weeghman Park for Charles Weeghman's Chicago Whales of the Federal League, which folded after the 1915 baseball season. The Cubs played their first home game at the park on April 20, 1916, defeating the Cincinnati Reds 7–6 in 11 innings. William Wrigley Jr. of the Wrigley Company acquired the Cubs in 1921. It was named Cubs Park from 1920 to 1926, before being renamed Wrigley Field in 1927. The stadium currently seats 41,649 people.
Medieval Torture Museum
Per their description, “We are the largest interactive historical museum in the U.S., occupying more than 6,000 square feet, with over 100 unique implements and devices on display. Enter the minds of fanatics, madmen, and murderers, and discover the world’s most detailed collection of confinement and torture devices. We believe that those who forget the past are doomed to repeat it, and have amassed an unprecedented collection of cruelty, based on historical documents and engravings, offering a chilling look into the darkest parts of human history. “
Sky Deck
Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower) with this pre-paid admission ticket. From the highest point in the city, look out on Chicago's skyline for panoramic views of the sprawling Windy City. Peruse the interactive displays and exhibits showcasing Chicago's history, which are geared toward curious learners of all ages. Then walk out on to the Ledge, a glass balcony that allows views of Navy Pier and Wrigley Field from one of the world's tallest buildings, standing 1,353 feet (412.4 meters) tall.
NOTE: The Ledge is not for everyone. We saw many a person have a tough time wanting to stand in the glass enclosure! But, fears aside, it is a super cool experience!
Walking Tours
Garfield Park Conservatory
In 1905, Chicago's West Park Commission's general superintendent and chief landscape architect, Jens Jensen, demolished three smaller conservatories in Humboldt, Douglass, and Garfield parks to create what was intended as "the largest publicly owned conservatory under one roof in the world" in Garfield Park. Many of the original plantings came from the three smaller Westside conservatories.
Constructed between 1906 and 1907, the Garfield Park Conservatory was designed by Jensen in collaboration with Prairie School architects Schmidt, Garden and Martin and the New York engineering firm of Hitchings and Company. It represents a unique collaboration of architects, engineers, landscape architects, sculptors, and artisans.
Jensen conceived the conservatory as a series of naturalistic landscapes under glass, a revolutionary idea at the time. The simple yet strong shape of the structure, which is meant to emulate the haystacks of the Midwest, complements the collection of plants and foliage that it houses.
In a hailstorm on the night of June 30, 2011, the conservatory suffered catastrophic damage to glass in showrooms, as well as production houses where plants are grown or stored. It took a full year to repair and replace all damage.
Today, the conservatory still follows the original tenets of Jensen.
Jackson Park
Jackson Park is a 551.5-acre park, located on the South Side of Chicago. The park was designed in 1871 by Frederick Law Olmsted and Calvert Vaux, then greatly remodeled in 1893 to serve as the site of the World's Columbian Exposition, making it one of the largest and most historically significant parks in the city.
Some of the park's features still reflect the fair's legacy, including a Japanese garden, the Statue of The Republic, and the Museum of Science and Industry. As part of the Woodlawn community area, it extends along Lake Michigan and borders Hyde Park and South Shore in the city.
Millenium Park
From 1852 until 1997, the Illinois Central Railroad owned a right-of-way between downtown Chicago and Lake Michigan, in the area that became Grant Park, using it for railroad tracks. In 1871, Union Base-Ball Grounds was built on part of the site (that became Millennium Park). The Chicago White Stockings played home games there until the grounds were destroyed in the Great Chicago Fire. Lake Front Park, the White Stockings' new ball grounds, was built in 1878 with a short right field due to the railroad tracks. The grounds were improved and the seating capacity was doubled in 1883, but the team had to move after the season ended the next year, as the federal government had given the city the land "with the stipulation that no commercial venture could use it". Daniel Burnham planned Grant Park around the Illinois Central Railroad property in his 1909 Plan of Chicago. Between 1917 and 1953, a prominent semicircle of paired Greek Doric-style columns (called a peristyle) was placed in this area of Grant Park (partially recreated in the new Millennium Park). In 1997, when the city gained airspace rights over the tracks, it decided to build a parking facility over them in the northwestern corner of Grant Park. Eventually, the city realized that a grand civic amenity might lure private dollars in a way that a municipal improvement, such as ordinary parking structure, would not and thus began the effort to create Millennium Park.
The 24.5 acre park opened in 2004 and intended to celebrate the third millennium. Featuring a variety of public art, outdoor spaces and venues, the park is bounded by Michigan Avenue, Randolph Street, Columbus Drive and East Monroe Drive.
Wandering
As always, wander around the city for your own (and free) tour! When you have a beautiful day like we did, you’ll be happy to just take it all in!
Why They Call It The “Windy City”
A History Summary
1671 - Potawatomi guides first took the French trader, Nicolas Perrot, to the Miami villages near the site of present-day Chicago.
1679 - In its earliest records, the Chicago area was inhabited by a number of Algonquian peoples, including the Mascouten and Miami. The name "Chicago" is derived from a French rendering of the Native American word shikaakwa, known to botanists as Allium tricoccum, from the Miami-Illinois language.
1683 - La Salle built Fort St. Louis on the Illinois River. Almost 2,000 Miami, including Weas and Piankeshaws, left the Chicago area to gather on the opposite shore at the Grand Village of the Illinois, seeking French protection from the Iroquois.
1688 - Henri Joutel noted that the wild garlic called, "chicagoua", grew abundantly in the area, henceforth the name of the city.
1790 - The first settler in Chicago was Jean Baptiste Point du Sable, a free black man, who built a farm at the mouth of the Chicago River. He left 10 years later.
1803 - 1837 - The U.S. built Fort Dearborn, on the Chicago River. It was destroyed by Indian forces during the War of 1812 in the Battle of Fort Dearborn, and many of the inhabitants were killed or taken prisoner. It was rebuilt in 1818 and used until 1837.
1829 - 1830 - The Illinois legislature appointed commissioners to locate a canal and lay out the surrounding town (at the time, there were only 100 people living in Chicago). On August 4, 1830, it was recognized as a town called, “Chicago”.
1833 - On August 12, 1833, the Town of Chicago was incorporated with a population of 350. It was also in this year that the Indian tribes were beginning to be forced to move west of the Mississippi River
1834 - On July 12, 1834, the Illinois from Sackets Harbor, New York, was the first commercial schooner to enter the harbor, a sign of the Great Lakes trade that would benefit both Chicago and New York state.
1837 - Chicago was granted a city charter by the State of Illinois.
1840 - The boom town had a population of over 4,000.
1848 - In 1848, the opening of the Illinois and Michigan Canal allowed shipping from the Great Lakes, through Chicago, to the Mississippi River and the Gulf of Mexico. The first rail line to Chicago, the Galena & Chicago Union Railroad, was completed the same year. It also became home to national retailers, offering catalog shopping, such as Montgomery Ward and Sears, Roebuck and Company, which used the transportation lines to ship all over the nation.
1850s - The construction of railroads made Chicago a major hub with over 30 lines entering the city. Also, hundreds of saloons had offered gambling opportunities, including off-track betting on the horses
1855 - The Know-Nothings elected Levi Boone, mayor, who banned Sunday sales of liquor and beer. His aggressive law enforcement sparked the Lager Beer Riot of April 1855, which erupted outside a courthouse.
1856 - The city council decided that the entire city should be elevated four to five feet by using a newly available jacking-up process. In one instance, the five-story Brigg's Hotel, weighing 22,000 tons, was lifted while it continued to operate.
1857 - Chicago was the largest city in what was then called, “the Northwest”. In 20 years, Chicago grew from 4,000 people to over 90,000.
1860 - The city had become the nation's trans-shipment and warehousing center.
1870s - Refrigerated cars were invented and heavily used in Chicago to transport meat.
1870 - 1890 - Chicago grew from a city of 299,000 to nearly 1.7 million and was the fastest-growing city in world history.
1871 - The Central Business District was destroyed in a fire. The damage from the fire was immense - 300 people died, 18,000 buildings were destroyed, and nearly 100,000 of the city's 300,000 residents were left homeless. How did this happen? Most of Chicago's buildings and sidewalks were then constructed of wood. Also, the lack of attention to proper waste disposal practices, which was sometimes deliberate to favor certain industries, left an abundance of flammable pollutants in the Chicago River, along which the fire spread from the south to the north. The fire led to the incorporation of stringent fire-safety codes, which included a strong preference for masonry construction.
1875 - During the election of April 23, 1875, the voters of Chicago chose to operate under the Illinois Cities and Villages Act of 1872. Chicago still operates under this act, in lieu of a charter.
1893 - The World's Columbian Exposition was constructed on former wetlands at the present location of Jackson Park, along Lake Michigan. The fair featured the first and until recently the largest Ferris wheel ever built.
1898 - 1942 - Albert Lasker, known as the "father of modern advertising," made Chicago his base from 1898 to 1942. As head of the Lord and Thomas agency, Lasker devised a copywriting technique that appealed directly to the psychology of the consumer. Women, who seldom smoked cigarettes, were told that if they smoked Lucky Strikes, they could stay slender. Lasker's use of radio, particularly with his campaigns for Palmolive soap, Pepsodent toothpaste, Kotex products, and Lucky Strike cigarettes, not only revolutionized the advertising industry but also significantly changed popular culture.
1903 - On December 30, 1903, the "absolutely fireproof", five-week-old Iroquois Theater was engulfed by fire. The fire lasted less than 30 minutes, killing 602 people as a result of being burned, asphyxiated, or trampled.
1915 - The S.S. Eastland was a cruise ship, based in Chicago, and used for tours. On July 24, 1915, the ship was boarding passengers when it rolled over while tied to a dock in the Chicago River. A total of 844 passengers and crew were killed. An investigation found that the Eastland had become too heavy with rescue gear that had been ordered by Congress in the wake of the Titanic disaster.
1919 - Progressive reformers in the business community created the Chicago Crime Commission (CCC) after an investigation into a robbery at a factory showed the city's criminal justice system was deficient. The CCC initially served as a watchdog of the justice system. After its suggestion that the city's justice system begin collecting criminal records was rejected, the CCC assumed a more active role in fighting crime. In addition that year, the Chicago race riot erupted, in what became known as "Red Summer" (38 people died and over 500 were injured), when other major cities also suffered mass racial violence based in competition for jobs and housing as the country tried to absorb veterans in the postwar years.
1920s - 1930s - New construction boomed in the 1920s, with notable landmarks, such as the Merchandise Mart and art deco Chicago Board of Trade Building, completed in 1930. The Wall Street Crash of 1929, the Great Depression, and diversion of resources into World War II led to the suspension of new construction for years. In addition, Bootleggers and smugglers bringing in liquor from Canada formed powerful gangs. They competed with each other for lucrative profits, and to evade the police, to bring liquor to speakeasies and private clients. The most notorious was Al Capone.
1928 - The CCC’s role expanded further after Frank J. Loesch became president in 1928. Loesch recognized the need to eliminate the glamor that Chicago's media typically attributed to criminals. Determined to expose the violence of the crime world, Loesch drafted a list of "public enemies"; among them was Al Capone, whom he made a scapegoat for widespread social problems.
1942-1943 - The world's first controlled nuclear reaction was conducted at the University of Chicago as part of the top secret Manhattan Project. In addition, steel mills in the city of Chicago, alone, accounted for 20% of all steel production in the United States and 10% of global production. By 1943, the city produced over $24 billion in wartime goods.
1950s - The postwar desire for new and improved housing, aided by new highways and commuter train lines, caused many middle and higher income Americans to begin to move from the inner-city of Chicago to the suburbs. Restructuring of the stockyards and steel industries led to massive job losses in the city for working-class people. The city population shrank by nearly 700,000.
1968 - After the assassination of Martin Luther King Jr., major riots of despair resulted in the burning down of sections of the black neighborhoods of the South and West sides. Protests against the Vietnam War at the 1968 Democratic National Convention, held in Chicago, resulted in street violence, with televised broadcasts of the Chicago police's beating of unarmed protesters.
1974 -The Sears Tower (now the Willis Tower) was completed at 1451 feet, the world's tallest building.
1992 - April 13, 1992, billions of dollars in damage was caused by the Chicago Flood when a hole was accidentally drilled into the long-abandoned Chicago Tunnel system, which was still connected to the basements of numerous buildings in the Loop. It flooded the central business district with 250 million US gallons of water from the Chicago River.
