36 Hours in Chicago

36 Hours in Chicago

Overlooking Chicago's Millennium Park

Architecturally eye-catching, culturally diverse, and full of culinary treats, the Windy City merges metropolitan glamour with Midwestern warmth and hospitality. Across over seventy unique neighborhoods—from Lincoln Park to The Loop—we're always astounded at the array of things to do. Be drawn in by public sculptures and sweeping skyscrapers, visit a park or two, take in the shores of Lake Michigan, and wander through the world-famous masterpieces at the Art Institute of Chicago. Since a quick visit really only scratches the surface of this lakeside city, here’s our advice on how to make the most of our 36 hours in Chicago.

Day 1

9 a.m.—Meander along the Magnificent Mile

We dive right into the heart of Chicago to start our first morning with a stroll along the Magnificent Mile (Michigan Avenue). These thirteen blocks, running from Oak Street in the north to the Chicago River in the south, will tantalize you with shops, restaurants, and beautiful buildings such as The Wrigley Building, and Tribune Tower. Grab a bite to eat, take in the stunning architecture, and perhaps take a riverside walk before brunch at one of the Mile's many eateries.


12 p.m.—A Stroll in Millennium Park

Making our way to the 24.5-acre Millennium Park, we'll start with an exploration of Cloud Gate—or as most people know it: The Bean. This 110-ton sculpture by Anish Kapoor, shaped rather like an enormous bean, has a polished surface that reflects the skyline, and we can waltz with our own shifting reflection underneath the sculpture. Millennium Park also features the playful Jaume Plensa’s Crown Fountain, as well as the iconic Jay Pritzker Pavilion and curving BP bridge, both designed by architect Frank Gehry. For a rooftop lunch we like to stop at Cindy’s, a restaurant atop the Chicago Athletic Association hotel where you can enjoy the sun and a panoramic view of Millennium Park and Lake Michigan.


2 p.m.—The Art Institute of Chicago

Escape the afternoon heat in the cool interiors of the world renowned Art Institute of Chicago. The building is guarded by two regal lions, and once we pass these fearsome protectors flanking the doors, we're awash is over 260,000 works of art. The collection includes masterpieces such as Seurat’s "Sunday Afternoon on the Island of La Grande Jatte," Hopper's "Nighthawks," Picasso's "Old Guitarist," and Warhol's "Four Mona Lisas." We think the best way to see the impressive (and overwhelming) collection is on a tour of the Art Institute with one of our art historians.


5 p.m.—Drinks with a View

For a sunset with a view—and, we mean a real view—we'll head up to the 95th floor of the former John Hancock Center in The Signature Room. While it can be crowded with tourists and locals alike, the sweeping 360-degree views of the Chicago skyline through floor-to-ceiling windows never fail to take our breath away (literally—don’t look down). 


8 p.m. – Laugh with Second City

Chicago has built a reputation for improv, and the cast at Second City’s Up Comedy Club proves why. A Chicago institution since the late 1950s, Second City is home to some of the best improv-based comedy shows in America, and they count among their alumni comedy names like Steve Carell, Stephen Colbert, Bill Murray, and Tina Fey. Catch an 8pm show and discover up-and-coming comedy talent, then stick around for a free improv set featuring cast members and (often famous) guests.

Another improv group that’s made a name for themselves in the Chicago comedy scene is the Improvised Shakespeare Company at the iO Theatre, where a talented troupe weave an off-the-cuff two-act Shakespearian masterpiece, based on an audience member title suggestion. 

Day 2

9 a.m.–Brunch in the Windy City

We'll start our second day with breakfast at Blue Door Farm Stand, a Lincoln Park staple serving a tidy mix of sweet and savory brunch options. This airy restaurant merges rustic exposed wood beams with more modern iron chandeliers and a marble bar for a nice blend of comfort and novelty. (For days when our sweet tooth is calling, we opt for their pancakes and candied pecans.) In the mood for French toast or waffles? Batter & Berries has a French toast flight that’s sure to delight, and their hash browns and maple chicken are on our list of favorites.

10 a.m. – The Museum of Contemporary Art Chicago

The Museum of Contemporary Art is often overlooked, but this collection of innovative exhibits is worth a visit. The building itself—designed by German rationalist architect Josef Paul Kleihues—is architecturally stunning, with an aluminum façade that nods to the works of Louis Sullivan and Dankmar Adler and a limestone base that references the iconic Water Tower and pumping station located nearby. The ellipsoid black granite staircase draws visitors up through the building and enhances the appreciation of the art on display.

12 p.m. – The Chicago History Museum

One of the quieter museums in the city is the Chicago History Museum, located at the southern end of Lincoln Park. The museum examines important events in the city's history from the impact of the first railway and Chicago’s vibrant blues scene, to the devastating effects of the Great Fire and the subsequent reconstruction efforts. Because we think one of the most important parts of visiting any city is understanding its history and contributions, this museum definitely deserves a place in your 36 hours in Chicago itinerary.

3 p.m. – Enjoy Lincoln Park

Leave the museum and stroll into the beautiful Lincoln Park—a reference to both an actual park and the surrounding tree-lined neighborhood. The area has something for everyone, from restaurants and fancy cocktail bars to some of Chicago's best beaches. The area also features the Lincoln Park Zoo and the Lincoln Park Conservatory. At night, people come to this neighborhood for live music and theater as well, including at the famous Steppenwolf.

7 p.m. – Find Chicago’s Best Deep Dish Pizza

New York City might have the best pizza in the world, but Chicago’s deep dish pizza is in a class of its own. Most guides will recommend stopping at Lou Malnati’s or Giordano’s, and while both these establishments serve great pizza, we usually find long lines and a tourist crowd. For the best deep dish pizza in Chicago, we'd highly recommend Pequod’s, where you’ll find fantastic deep dish pizza and a genuinely local experience.

9 p.m. – Look for a Hidden Speakeasy

We'll (night)cap off our last night in the city with a drink at an authentic '20s era speakeasy. Look for a secret bookcase door in the Green Door Tavern and descend into a whole new world at The Drifter, where we like to sip cocktails served on tarot cards and enjoy an evening of entertainment. Their rotating menu has over 100 cocktails, and we've never failed to find something exceptional to sip.

11 p.m. – A Night of Jazz

The night’s not over we catch some live jazz at the iconic Green Mill Cocktail Lounge, where strains of soulful jazz soothe our nerves every night of the week. Traditional jazz, bebop, and improv all have their place here, and music plays on into the early morning hours in the hands of phenomenal artists such as Von Freeman, Kurt Elling, and Orbert Davis. We see glimpses of Al Capone’s influence in the art nouveau décor, embellished woodwork, and wall memorabilia ... as well as the booth where he and his henchmen would enjoy a drink while keeping an eye on the door.

More Things to do in Chicago

Are you spending another day in the city, or already planning your next visit? 36 hours barely scratches the surface of things to do in Chicago, and if you have more time in the city, we also recommend visiting the National Museum of Mexican Art, the surrounding Pilsen neighborhood, and the American Writers Museum.

Keep in mind that Context offers private tours with local experts to give you an insider’s perspective on the art, architecture, and history that make Chicago such a fascinating city.

Want to learn with a true expert? Get a comprehensive view with one of Context's tours, or learn more about your favorite destination or topic with our virtual, live-taught courses and seminars

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