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What to Do With a Day in Chicago?

Chicago Insider Guides
by Katie Scott Aiton Feb 20, 2018

Planning an itinerary that highlights the best of what a city has to offer in just 24-hours can be daunting. If you have a short window, sunrise to sunset, you need local advice to make sure you don’t miss out.

We pulled together top tips from Chicagoans. Here’s what they have suggested to do with a day in the Windy City.

What to do with a day in Chicago

1. Where to eat
2. Where to drink
3. Entertainment
4. Cultural activities
5. Outdoor activities

1. Where to eat

With regards to one of Chicago’s most iconic dishes, pizza, there seems to be a running theme that any local pizza joint would be a safe bet. That said, Richa Agarwal suggests “the deep dish pizza at Pizzeria Uno.” Mike Manly lists off “Pizano’s on either Madison (about a block from the Art Institute) or on State Street (800 north). Pizano’s, Pizzeria Uno, Due, and Lou Malnati’s are all great.”

If you are looking for a quick eat, Dan Pepper recommends Manny’s Deli: “this storied, old-fashioned, self-service deli in the South Loop is ground zero for Chicago politics, which gained national prominence with the election of President Obama in 2008.” Nycole Hampton also suggests ordering a quick bite at the bar at Cochon Volant, specifcally the cheese burger.

If you’re visiting during the summer months, Chris Wake says “there are a ton of outdoor spots to grab food or a drink. Lincoln Park and near north may be crowded, but there are equally good or better spots in the near west (Wicker Park, Bucktown, Roscoe Village, etc.).”

For brunch, Nycole Hampton, suggests the shellfish and seafood stations at Shaws Crab House. With regards to seafood, she also recomments the oysters at Eatarly, shrimp and grits from GT Fish & Oyster, and the seafood tower from Cold Storage.

If you have a sweet tooth there are many options, Nycole Hampton suggests that you head to Do-Rite Donuts for apple fritters, icecream from Rainbow Cone, and cookies that are the size of your face from Summer House Santa Monica. She adds that you should not skip the 14k chocolate cake from RPM Steak.

2. Where to drink

John Meyers suggests that you “Grab a drink at the Signature Room at the top of the Hancock Center. Fantastic views of Chicagoland and Lake Michigan.”

Richa Agarwal also recommends enjoying the view at the Vertigo Sky Lounge.

Jennifer Billock has this to say, “We may have our share of ritzy places to get a drink, but we’re also founded on working class ideals, so we know how to enjoy a good dive, too. For a night out on the town (a cheap night), we know better than to get all dressed up and head to rooftops and hotel lounges. We put on jeans and a t-shirt and go to the neighborhoods.” Jennifer’s top 7 dive bars are, The Victor Bar, Happy Village, L&L Tavern, Map Room, Slippery Slope, The Heavy Feather and Schubas Tavern.

3. Entertainment

According to Rishi Natarajan, “Chicago has a variety of comedy shows that are of particularly good quality and often are the platform from which national comedy stars arise. In particular, Second City in Chicago is a phenomenal comedy theatre with hilarious shows… if you’re into comedy at all, definitely add this to your list.”

Locals also suggest that the shopping in Chicago is good, especially in the summertime. Natarajan says, “Chicago’s famous Magnificent Mile is a 1 mile stretch of Michigan Avenue that’s lined with stores (think the Chicago equivalent of New York’s 5th Avenue).”

When it comes to live music, Natarajan explains, “There are a lot of long-running music venues in the city that are worth visiting. The Chicago Symphony Orchestra is one of the Big Five orchestras and is a pleasure to listen to. Chicago also has several good Jazz/Blues venues, if that’s of interest.” Local Lauren Victoria adds “Blues music has a rich history in Chicago, and you can get acquainted every night at B.L.U.E.S. on Halsted. Performers range from new artists to national legends, both equally enjoyed by the audience. The venue is small and can get quite crowded, so arriving early is always a good plan. If you visit on a Sunday, your ticket gets you free entrance to Kingston Mines — another famous blues bar down the street.”

Victoria goes on to add, “Did you know that Chicago is the birthplace of the poetry slam? In 1984, the competition was started to showcase the city’s diverse talent. More than 30 years later, the tradition lives on. Every Sunday from 7 to 10 PM, poets from all across the country recite their best work over the smooth sounds of The Green Mill Quartet at the Green Mill Cocktail Lounge. You can also expect a special musical performance from a featured guest at intermission.”

Chris Wake states that your schedule should include a baseball game and offers this tip, “Cubs for the beer, the atmosphere in Wrigley and the fans, or White Sox for the hot dogs.”

4. Cultural activities

Here are some of the recommended stand-out museums in the city.

Rishi Natarajan remarks, “Chicago has a variety of excellent museums that you might consider visiting:

  • The Museum of Science and Industry is the largest science museum in the country and has all sorts of cool (and nerdy) exhibits (a U-505 German submarine exhibit, a NASA spacecraft, a working coal mine, etc.).
  • The Art Institute of Chicago is a fine art museum that I think is known for its collection of Impressionist art and is the 2nd biggest art museum in the US (behind the MoMA in NYC).
  • The Field Museum of Natural History will definitely appeal to those interested in the natural sciences. It has over 20 million specimens.”

Paul Beyer also suggests The Adler Planetarium, “The Adler Planetarium is a public museum dedicated to the study of astronomy and astrophysics. It was founded in 1930 by Chicago business leader Max Adler.”

5. Outdoor activities

Depending on what time of year you are visiting Chicago, there are many green spaces to enjoy.

Richa Agarwal recommends a “walk through Millennium Park and especially the adjacent Grant Park for the gorgeous Buckingham Fountain.” Agarwal continues, “if it’s hot, enjoy the palm trees and Lake Michigan at Oak St. beach. And/or one of the river/lake boat tours.” She adds, “If you’re a runner, you can see much more. Running along the Chicago River to the lakefront is really awesome, and there are miles and miles of scenic lakeshore to run along. You can also rent a bike.”

Lauren Victoria favors Garfield Park Conservatory for it’s “stark contrast to the urban city, the lush trees and colorful flowers create a perfect nature escape. With just a small donation of your choice, explore an array of plants from countries from all around the world. It’s also a great place to take the kids — there are educational events offered everyday.”

When it comes to where to get the best view of the city, most Chicagoans recommend Navy Pier.

Dan Pepper comments, “the Pier offers the most expansive views of the Chicago skyline — especially from the 150-foot Ferris Wheel, which rotates slowly.” Pepper also suggests the riverwalk where you can “take this promenade along the Chicago River from Navy Pier to Michigan Avenue.” And the water taxi, which he says is very cheap and offers cool views over the river. Mike Manley also recommends taking a boat on the water and adds, “Chicago Architectural Foundation’s river tour of Chicago architecture only takes an hour and gives you lots of great information about the city, as well as wonderful views of lots of great city landmarks from the water. You can board the boat down the steps to the Chicago River at the northeast corner of Michigan Ave. and Wacker Drive.”

Find some of these spots on our travelstoke map:

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