Traveling to Chicago: A First-Time Visitors Guide

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Advisor - Samar Asfour
Curated By

Samar Asfour

  • Chicago

  • Arts & Culture

  • City Travel

  • Solo Travel

  • Local Culture

  • Local Food

  • Entertainment

An aerial view of a coastal cityscape during twilight showcases the shoreline, buildings, and a road alongside the beach.
Curator’s statement

I've lived in Chicago for the past 21 years, but until a few years ago, I had no idea what an amazing city it was. Throughout the year, Chicago provides a plethora of activities and attractions for tourists of all ages and interests! Though the summer is the best time to visit, especially if it's your first time, the winter months are jam-packed with activities like festivals and Christmas markets. Everyone should visit Chicago at least once, in my opinion, as it boasts the most breathtaking skyline, a lovely beach (lake) and the best cafés and restaurants.

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Where to stay in Chicago

The St. Regis Chicago

A luxurious and iconic hotel offering an unparalleled experience in the heart of the Windy City.

Fora Perks
  • ★

    $100 hotel / resort credit.

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    VIP welcome & amenity.

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    Breakfast daily.

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    Upgrade & extended check-in/out whenever possible.

Nobu Hotel Chicago

Nobu Hotel Chicago: where luxury meets culinary excellence in the heart of the Windy City.

Fora Perks
  • ★

    Welcome amenity.

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    $60 breakfast credit daily.

  • ★

    Upgrade & extended check-in/out whenever possible.

Pendry Chicago

A contemporary luxury hotel is set within the iconic 1929 Art Deco Carbide & Carbon Building in Chicago’s Loop neighborhood.

Fora Perks
  • ★

    $100 hotel credit.

  • ★

    Breakfast daily.

  • ★

    Upgrade & extended check-in/out whenever possible.

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.

Arlo Chicago

Nestled in the heart of the Windy City, this chic urban retreat offers a perfect blend of modern comfort and local charm.

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Things to do in Chicago

A cityscape with skyscrapers beside a body of water during sunset.

Must-see attractions in Chicago:

  • Willis Tower for the Skydeck

  • The John Hancock Tower's 360 Chicago Observation Deck: If you're pressed for time, I'd choose this over the Skydeck because it offers better views of the city, and you can do the iconic "Tilt" here. Visit around sunset and sip a drink while taking in the scenery!

  • Navy Pier: An ideal spot to experience thrilling rides and city sights with a group of friends or if you have kids. Love the views of the Ferris wheel! From here, you can go on a boat tour or take the Chicago Water Taxi to the main city for a quick ride experience.

  • Millennium Park - two words: The Bean (Cloud Gate)

  • Other things to do in this area: Jay Pritzker Pavilion - watch movies or music performances based on availability, get wet at the Crown Fountain, walk (or run) through the Maggie Daley Park, Ice skating in the winter!!

Visit a museum:

  • Art Institute of Chicago: If you love art, this place is a must.

  • The Field Museum, the Shedd Aquarium, the Planetarium (my favorite). Somedays of the month are offered for free.

  • Interactive museums: The WNDR Museum, Museum of Ice Cream and Museum of Illusions.

  • Magnificent Mile — If you're feeling a bit bougie, grab a credit card and come shop on this street.

While you're there, take a boat tour of the Chicago Architecture Center to learn about the city's iconic skyline.

  • Chicago Riverwalk — Take a walk along the Chicago Riverwalk, a scenic walkway that winds along the Chicago River.

  • See a game at Wrigley Field — Home of the Chicago Cubs, or Soldier Field, home of the Chicago Bears.

Neighborhoods

  • Chinatown - Can't go wrong with some dumplings and matcha.

  • Little Italy - Small spot for Italian Ice is amazing

  • Greektown- Get some gyros!!!

  • Pilsen - amazing area for some birria tacos.

Day trips:

  • Bridgeview - About 35 minutes away from the city, this is little Palestine, boasting with Mediterranean restaurants and local coffee shops.

  • Naperville - Downtown Naperville is a nice getaway from the city, while still enjoying local shops.

Places to eat & drink in Chicago

A close-up image of a deep dish pizza.

Cafes:

  • Nomad

  • Ground Up

  • Beatrix

  • Maison Marcel

  • 3 Arts Club Cafe

  • Oud Coffee & Cafe.

Rooftops:

  • Cindy's rooftop

  • Chateau Carbide at the Pendry

  • Nobu Chicago Rooftop

  • Boleo Rooftop Bar at the Kimpton Grey Chicago

Deep-dish pizza:

  • Giordano's

  • Lou Malnati's

  • Gino's East.

Other unique favorites of mine:

  • Lyra - Greek restaurant, my favorite thing here is the dips and pita bread and the Octopus!

  • Beity - Michelin-star Lebanese restaurant for that special occasion.

  • Beatnik on the river - Great views, day or night and a unique experience with a unique menu.

  • Andros Taverna - Best Greek food!

  • Time Out Market

Chicago hot dogs!

Advisor - Samar Asfour

Travel Advisor

Samar Asfour

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This guide is a part of our ongoing series on travel to Chicago. Looking for more travel inspiration? Check out my guide, Four days in Nice, France and the French Riviera