Foodie's Guide to Attractions & Restaurants in Chicago

Fora travel advisor Elizabeth Callaway wearing red sweatshirt and black jacket stands in front of colorful field of tulips
Curated By

Lizz Callaway

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  • Domestic Travel

  • USA

  • Chicago

  • Arts & Culture

  • City Travel

  • Couples Travel

  • Food & Wine

  • Group Travel

  • Foodie

  • Architecture

  • Museums

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Curator’s statement

Chicago, Illinois is full of history, diversity and more to explore than you can cover in a weekend. Some of the most famous works of art, delicious bites and inventive drinks can be found here. Here are my favorite things to do and places to eat when visiting the Windy City.

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Where to stay

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The Peninsula Chicago

Elegant luxury hotel located in a high-rise in downtown Chicago.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Chicago Athletic Association - The Unbound Collection by Hyatt

Chic hotel with a fun vintage sports theme set in a historic building overlooking Chicago's Millennium Park.

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  • Hotel / resort credit.

  • Breakfast daily.

  • Welcome amenity

  • Upgrade & extended check-in/out whenever possible.

Kimpton Gray Hotel

Beautiful design-forward hotel featuring city views in Chicago's financial district.

Fora Perks
  • $50 hotel / resort credit.

  • Bottled water and fresh fruit / snacks in room upon arrival.

  • Upgrade & extended check-in/out whenever possible.

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Fora travel advisor Elizabeth Callaway wearing red sweatshirt and black jacket stands in front of colorful field of tulips

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Day 1: Arrive in Chicago

Aerial view of tall buildings next to body of water during daytime

If you are landing at O'Hare, note that the trip into town can be long, busy and potentially expensive if surge pricing on ride shares applies.

Transportation Options:
Taxi - Time: 25 minutes (longer during rush hour). Cost: ~$45. Location: Outside the baggage claim doors of each of the terminals

Uber/Lyft- Time: 25 minutes (longer during rush hour). Cost: ~$45 but subject to surge pricing. Location: Request for certain locations on the departure level

Public transportation - Time: 45 minutes. Cost: ~$5. Location: Underground, in the center of terminals 1,2 and 3. From the international terminal, take the free O'Hare train to reach the blue line train station.

Check into your hotel and head out for a bite.

I highly recommend grabbing a table at Girl and The Goat or Au Cheval to properly kick off your trip - you won't regret it.

Day 2: Explore Millennium Park and The Art Institute

People walking around large silver structure with buildings in the background during daytime

Rise and Shine!

If you had a chance to explore bars like Federales or Bandit after Girl and the Goat, you may want something refreshing. Goddess and the Baker has fresh-pressed juices, bagels, and whole grain bowls to help you get ready for the day.

Head over to Millennium Park and wander around the attractions, including Cloud Gate, also known as The Bean.

Walk towards the tall lion statues in front of The Art Institute of Chicago and immerse yourself in the priceless works of art on display. From classics like Monet's Water Lillies, Nighthawks and A Sunday on La Grande Jatte to new installations like the Obama Portraits and Warhol's Marilyn Monroe. Pro Tip: you can download the app to see peak times, self-guided tours and more.

Grab a classic Chicago hot dog at Portillo's or head to my controversial pick for best deep dish: Pequod's.

Day 3: Boat tour & dinner at Giant

Body of water lined by tall buildings during daytime

Put your sunscreen, hat, and sunglasses on and hop on an architectural boat tour. Along the river, you can see some of the most beautiful and unique skyscrapers in the world. Walk across DuSable Bridge and you will be able to find numerous companies with tours leaving multiple times per day. Pro Tip: make sure to give yourself some flexibility on timing because there could be delays depending on boat traffic.

After the boat, head over to Hancock Center and ride the elevator to the top for 360 Chicago. Panoramic views of the city, Lake Michigan and more are worth the ride. If you're brave enough, buy a ticket for The Tilt and lean over the edge of the building in this daring experience.

For pre-dinner drinks, head to your reservation at The Aviary in The West Loop. Enjoy a 3-course cocktail progression in one of the most innovative restaurants in the country. Ever had a negroni with a slingshot and a high-end walking taco?

Continue your evening of eating by hopping in a car, head to Logan Square and to your dinner at Giant. A recent addition to the Michelin Guide, Giant is the baby of Jason Vincent and provides the familiar as well as pushing the boundaries.

Properly full of Giant, wander next door to Scofflaw for a dark, steam-punk vibe of a cocktail bar. They not only have the Chicago favorite, Malort, on draft, but they are also known for their gin cocktails. Pro tip: they pass around fresh, warm chocolate chip cookies at midnight.

Day 4: Catch a game at Wrigley Field or explore more of the city

Large red sign during daytime

More time in town? Depending on the time of year, grab tickets for a game at Wrigley Field and enjoy the bars, restaurants and crowds around Wrigleyville.

Sports not your thing? The beaches, water, endless museums and more will fill your day and leave you wanting more time in town.

Need to Know

Hungry for more travel inspo? Check out my guide to Seattle: Foodie's Guide to the Best Restaurants in Seattle.

Fora travel advisor Elizabeth Callaway wearing red sweatshirt and black jacket stands in front of colorful field of tulips

Travel Advisor

Lizz Callaway

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