32 ways to take on Chicago

Chicago is a true modern metropolis with both a rich history and a laid-back Midwestern vibe. Grab a bite of nostalgia with a dog at Wrigley Field and then jump into this list of the top 32 things to do while you’re in town.

The Bean – photo via @sheikher


What to see:

  • Field Museum – one of the largest natural history museums in the world, the Field Museum attracts 2M+ visitors annually. Its neo-Classical buildings (built in 1893 as part of the World’s Columbian Exposition) house everything from animal exhibitions, deep looks into Ancient Egypt (including 23 human mummies & a replica of the tomb or Unis-Ankh), and the DNA Discovery Center (where visitors can watch real scientists extract DA from a variety of organisms).
  • The Art Institute – one of the oldest and largest museums in the US, the Art Institute of Chicago is easy to get lost in. Wander through the largest collection of impressionist work outside of Paris, explore more contemporary art in the Modern Wing, or one of the 30+ special exhibitions each year.
  • Frank Lloyd Wright architecture tour – Chicago is packed with Frank Lloyd Wright landmarks: his first Home & Studio in Oak Park, the Frederick C Robie House (one of the most important buildings in American architectural history), the Rookery in the heart of Chicago’s financial district, Unity Temple (the only surviving public building from his Prairie period), and more. Pick a tour that will show them all to you in one long day, or explore them piece-by-piece.
  • The Shedd Aquarium – Just nearby the Field Museum lies the Shedd Aquarium, a giant indoor aquarium holding more than 32,000 aquatic animals. Don’t miss the dolphin show.
  • Baha’i Temple – free and open to all, this building is the oldest surviving Baha’i House of Worship (there are only eight in the world). Come to enjoy the jaw-dropping architecture and grounds (the building took 30 years to complete) and stay to learn a bit more about this Buddhist faith.
  • Get a view:
    • Willis Tower Sky Deck – float on air (or at least feel like you are) at the Willis Tower Sky Deck. If you’re brave enough, step out onto the glass-bottomed deck on the 103rd floor to catch a bird’s eye view of the surrounding 4 states.
    • 360 Chicago Observation Deck & Tilt – Not for the faint of heart, the TILT will literally tilt you out until you have a downward-facing view 1000 ft above the Magnificent Mile. For those a bit less adventurous, just head to the observation deck where you can see the sights from the comfort of solid ground.


Willis Tower Skydeck – photo via @miliiicash


What to do:

  • Millennium Park – originally built as a monument to the second millennium, this park has plenty to explore. See your reflection in the Bean, watch the tree lighting during the holidays, or plan for one of the space’s many special events. Want a little more excitement? Pick up a bike rental and jump on the Lake Shore Trail (an 18-mile path spanning multiple parks along the west side of Lake Michigan).
  • Magnificent Mile – an upscale section of Michigan Ave, the Mag Mile has several of the tallest skyscrapers in America, many landmarks (such as Water Tower Place), and plenty of shopping.
  • Explore Navy Pier – don’t let the fact that this is Chicago’s biggest tourist attraction dissuade you from visiting. Grab some food at the Family Pavilion (anything from Creole & Jazz-themed restaurants to a fully-stocked Food Court), ride the ferris wheel, or just hang out in the Beer Garden.
  • Catch some sports:
    • Cubs game at Wrigley Field
    • Bulls game at United Center
    • Blackhawks (also at United Center)
    • Bears Game at Soldier Field
  • North Ave Beach – see what some would call the best view of the city and do any number of outdoor activities: beach volleyball, games of frisbee, biking, stand-up paddle boarding, or simply jumping in Lake Michigan for a swim.
  • Take a Riverboat Architecture Tour – Chicago is well-known for its architecture so what better way to get an up-close look than from a riverboat cruise? See more than 40 points of interest from renowned architects like Miles van der Rohe, Helmut Jahn & Louis Skidmore.
  • Summer festivals – Summer is prime festival season in Chicago so you’re sure to find one no matter when you visit. Some of our faves? Taste of Chicago (free food + music sounds like a win-win), Chicago Blues Festival (the largest blues festival in the world), Lollapalooza, & the Chicago Jazz Festival. And coming up this weekend is the Pitchfork Music Festival.
Millennium Park – photo via @adela.stroh.flow


Where to eat:

With everything from the famous deep dish pizzas to Michelan-star restaurants, when it comes to food, everyone will leave happy.

  • Au Cheval – all you need to know? Order the burger because it’s the best. The single cheeseburger is the most popular: two patties, melted cheese, mayo, and pickles. Simple perfection. And if you’re feeling adventurous, be sure to add on the thick-cut bacon and/or an egg.
  • Gibsons – Gibsons is the best steakhouse in Chicago (fun fact: it’s the only restaurant group to be awarded its own USDA Prime Certification for beef). We recommend getting the Filet Mignon (you are at a steakhouse after all) with a side of brussell sprouts (to make you feel like you’re being healthy even though these are covered in bourbon butter & bacon pieces).
  • Girl and the Goat – Top Chef season 4 winner Stephanie Izard opened this restaurant focusing on Mediterranean shared-plates and local ingredients. The menu (divided between Meat, Fish, & Vegetables) shifts with the seasons but one of our favorites are the goat empanadas (with an avocado smash & grilled pineapple-blueberry salsa, these are to die for). Definitely make a reservation—this place is popular.
  • Tango Sur – An Argentinian steakhouse with a price point that won’t empty your wallet. Get the empanadas and the provoleta (provolone cheese grilled with olive oil & roasted peppers) to start and the El Filet (fillet mignon grilled and then topped with red onion wine sauce & spinach mashed potatoes).
  • Pequod’s – ask around for the best deep dish pizza and Pequod’s name will definitely come up. The pizza is hot, the tomato sauce is perfectly tangy without being too acidic, and the thick crust is caramelized from cheese. Be prepared to wait (just know that its worth it).
  • Johnnie’s Beef – a local fixture for Italian beef, Johnnie’s has been making these juicy sandwiches for years. Get the original and wash it down with an Italian ice. Hot tip: it’s cash only so bring some money.
  • Superdawg – their signature dog is served Chicago-style (i.e. a poppy seed bun topped with mustard, relish, onion, green tomato, a pickle wedge, sport peppers, and served with plenty of crinkle fries). There’s a reason it’s been open since 1948.


Chicago pizza – photo via @aanotherusername


Where to drink:

  • Intelligentsia – a local coffee roaster that has made a name for itself nationwide, Intelligentsia will brew you up the perfect cup of coffee whether you’re looking for a latté or simply an espresso. If you’re looking for something a bit outside the box, try the carbonated turmeric cold brew—it’s the perfect refresher for a hot Chicago day.
  • Pickwick Coffee Roasting – Pickwick has a cozy location seemingly tucked between two buildings. Grab a latté and enjoy while sitting on the outdoor patio.
  • Lagunitas Brewing Company – Lagunitas’ blacklight-lit entrance hallway is a bold statement proclaiming you’re not just at any brewery. Try a to snag a guided tour and end it with a flight.
  • Rec Room – This bar, with its worn seating, board games, and throwback jams feels like the basement you all hung out in in high school (in a good way). But don’t let that fool you, it turns into a party.
  • LH Rooftop – come for drinks at this 22nd floor rooftop bar. Our favorite is the Roaring Twenties–strawberry & jasmine tea preserve topped off with champagne.
Oysters and drinks at 360 Chicago (formerly John Hancock Center) – photo via @dubaj21


Where to Stay:

Your best bet for a neighborhood is going to be the Magnificent Mile as it contains many of Chicago’s biggest attractions. Go to West Loop for a trendy, upscale vibe or River North for its steakhouses and bars.

  • Sofitel Chicago – Located on the Magnificent Mile, the Sofitel is minutes from the Water Tower, Tribune Tower, and Wrigley Building.
  • The James – A modern hotel with a hip vibe in the center of it all on the Magnificent Mile. Fun perk? Free bike rentals.
  • The Godfrey Hotel – The Godfrey is also in the North Side close to many of Chicago’s attractions. Plus, it has many amenities including a rooftop terrace, nightclub, and spa.



Tips for your stay?

  • To get around, either rent a car, rideshare, or use the local CTA.
  • Come during summer to take advantage of all the music festivals and street fairs.


Magnificent Mile – photo via @tayloromackie


  1. Holly

    I’m surprised a California brewery made the list instead if an actual Chicago brewery like Revolution Brewing.

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