Ask anyone about visiting Chicago and they’ll tell you it’s a lovely place to visit in summer. Winters are frigid, snowy, and any time you think it’s starting to warm up, a gust of wind will chill you to your core. Winters are not for the faint of heart, but they’re still my favorite time to visit Chicago. When it’s just you and the locals, you’re more likely to meet city residents, discover insider destinations, and fall in love with authentic Chicago.
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Remember, residents spend all year here, so the city incorporates all four seasons into its design. The Chicago Pedway, ignored by most visitors, is the perfect solution to traversing the city in winter. With over five miles of underground tunnels and covered bridges, there’s no reason to layer up and face the elements. Start your trip with a free guided tour of the Pedway to get the lay of the land and to discover hidden sites along the way; it’s more than just tunnels.
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Many Chicago visitors appreciate the city architecture on boat cruises and walking tours during the summer, but in winter you can focus on interior touches and art downtown, or head to Oak Park for guided tours of Frank Lloyd Wright homes.
While the Pedway is great for getting around, winter is also the perfect time to sample Chicago’s best restaurants. When it’s cold and dark out, you won’t even feel guilty for spending half your travels indoors! Every February, Chicago celebrates its culinary scene with Chicago Restaurant Week: ironically fourteen full days of prix fixe menus at top restaurants starting at $22 for lunch or $33-44 for dinner. For something more casual, head into Chicago neighborhoods like Wicker Park for budget-friendly meals.
Like most cities, tourism slows down in the winter and that’s a great thing! With smaller crowds and special deals at city sites, it’s easier to enjoy Chicago museums and attractions. Plan at least a day for Museum Campus, home to the Adler Planetarium, Field Museum of Natural History, and Shedd Aquarium. The planetarium in particular holds special events, like nighttime stargazing and evening happy hours. However, if museums aren’t normally your cup of tea, there are more interactive activities in Chicago, like learning how to make your own deep dish pizza.
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Admittedly, the first reason I even tried a trip to Chicago in the winter was just to take advantage of cheap Chicago hotels. My favorite hotel, Wit Chicago – a Doubletree by Hilton Hotel, averages around $129 per night in the winter despite being a modern property with deluxe amenities, a fantastic restaurant, and prime location. However, the city has plenty of unique hotels to add a fun twist to your stay!
Just because it’s cold and windy in the winter, don’t avoid Chicago. Not only is it enjoyable all year round, but winter is a great time to visit!
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