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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Things to do in Chicago
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
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!
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