Best Things to Do in Chicago

If you plan to go on a domestic trip this year or even next year, you're not alone; 65% of Americans do, too. After being in lockdown for so long, that desire to travel makes complete sense. But if you haven't decided where to go, consider a weekend in Chicago, Illinois. It's been the “Best Big City” in the United States for six consecutive years. Don't worry if you're unsure what to do or see when you visit Windy City; we're here to help you because there are countless activities in Chicago. Below, we've outlined the top things to do in Chicago while you're there for a weekend, so keep reading. We hope this Best Things to Do in Chicago post inspires you. 

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Best Things to Do in Chicago

Summer Activities Perfect for All Ages in Chicago

Anytime from April through May or September to October are the best times to visit Chicago. The temperatures during these times are warm enough to be comfortable and tolerable. These months also often have festivals lined up, but the crowds remain manageable. As for summer, it's Chicago's peak tourist season, so more festivals take place then. Trip planning during this time means paying more for lodging, though. The upside is you can avoid Windy City's November to March frigid temperatures.

Speaking of temperatures, always remember that they can change over time. This is especially true for cities like Chicago. Forecasters say Windy City has a weather that's harder to predict than others. So as part of your savvy vacation planning, regularly check the weather forecast. That way you can bring appropriate outfits based on the predictions. Check the weather forecast at least five days before your intended arrival. Five-day weather predictions are accurate about 90% of the time. Check it one last time before you head off (you might have to bring a raincoat, just in case).

Chicago is such a diverse city with a wide variety of activities from theater and comedy shows to a riverboat architecture tour and gangsters & ghosts tours, the city of Chicago offers something for everyone. 

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Best Things to Do in Chicago

Plan to Stay in the Loop

The Loop is one of the best areas to stay when you visit Chicago and are looking for a good Chicago hotel, especially for the first time. Also known as Chicago Loop or Chicago Downtown, the Loop is at the heart of town. You can easily travel to other parts of Windy City to do some sightseeing from here so it's best to pick a downtown Chicago hotel.

CityGO Chicago aka Go City Chicago

Start Your Weekend With a Decadent Breakfast

If you're arriving in Chicago early morning, grab some breakfast at one of the Loop's best bakeries. Many open early, from 7:30 AM, and offer energy-boosting baked goods and coffee. Stan's Donuts and Coffee, Goddess and the Baker, and Coralie Coffee are some of your top options.

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Best Things to Do in Chicago

Outdoor Adventure: Work off Your Breakfast at Millennium Park

Millennium Park, under half a mile from the Loop, is one of the world's most extensive green roofs. This 24-acre “roof” sits atop a railroad yard and massive parking garages.A walk to Millennium Park from the Loop is a great way to exercise in the morning. You can work off some of your breakfast calories during the under-10-minute walk. Then, burn even more as you go around the massive green space.

The park offers some of the best things to do in Chicago, such as a photo-op at Cloud Gate. Cloud Gate is one of the world's largest permanent outdoor art installations. More affectionately called The Bean, it's a masterpiece that boasts a stainless-steel surface. It reflects the surrounding city skyline and lights. Your trip to Chicago won't be complete without a selfie in front of this art installation.

Things To Do in Chicago for Couples

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After your photo-op, head to the Jay Pritzker Pavilion, another architectural wonder. It stands 120 feet above the ground in all its brushed stainless-steel glory. It's a majestic outdoor concert venue for afternoon or night shows, often for free. From the pavilion, go south to see the beautiful flora featured at the 3.5-acre Lurie Garden. Afterward, head west to the Crown Fountain, another impressive outdoor art installation.

Lunch Like a Local

At this point, you're likely hungry, so have lunch at one of the restaurants on South Michigan Avenue. You can go to The Gage or Cherry Circle Room for American food. You can also go for Asian at the Flat Top Grill.

Appreciate Art at the Art Institute of Chicago

The Art Institute of Chicago, founded in 1879, is one of the world's largest museums. It's a five-minute walk from the south of the Crown Fountain. It's home to an extraordinary collection of objects, including nearly 300,000 works of art. Here, you can find masterpieces from Pablo Picasso, Edward Hopper, and Grant Wood, to name a few. General admission to the fine arts institution costs $32 for out-of-state folks. However, it offers a discounted rate of $26 for seniors, students, and teenagers. Children 13 and under can get in for free.

Check out CityPASS Chicago

Check Out the Magnificent Mile

If your trip to Windy City involves shopping, the Magnificent Mile is one of the best places to do so. Also called Mag Mile for short, it's the city's primary commercial district. Here you can find hundreds of retailers, from Nordstrom to Neiman and Bloomingdale's.

If your wallet can't take much of a beating, don't worry; Mag Mile isn't all about shopping. It's also the location of some of Chicago's most famous landmarks, such as the DuSable Bridge. You can also find Wrigley Building, Tribune Tower, and Water Tower here, among many others.

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Best Things to Do in Chicago

Get on a Boat for a River Cruise

If you're still up for more activities in Chicago, you can go on an evening architecture Chicago river cruise. It's worth it since it's an informative tour of the city's incredible architecture. Plus, you can have some cocktails on the boat. The trained boat crew will share stories about the buildings during the cruise. You, in turn, will find yourself fascinated by their history. The tour can run from 75 to 90 minutes, depending on weather conditions. Alternatively, you can go on a fireworks river cruise the following day.

Try the Famous Chicago-Style Pizza

If you love pizza, you should grab a slice of none other than the Chicago-style pizza for dinner. That way, you can experience this dish in all its authenticity. Pequod's, Lou Malnati's, and George's all serve this decadent treat.

You can also head to the Italian Village by the Loop if you'd like a more Italian vibe for your fun activities Chicago. Here, you can enjoy traditional Northern Italian cuisine. Nearby are bars and taverns, including The Dearborn and the Cochon Volant. Have a few drinks here if you want before returning to your lodging.

Hilton Chicago

Break Your Fast on Day 2

Start your second day in Chicago with a delightful brunch at Cindy's Rooftop. It's on the 13th floor of the historic Chicago Athletic Association Hotel. The hotel building itself is a sight to see, thanks to it being an architectural wonder. Another excellent option is The Atwood by the Loop. It offers tasty all-day American cuisine. You can also drop by here later for an afternoon cocktail.

Explore Natural History at the Field Museum

The Field Museum is one of the world's oldest natural history museums, dating back to 1894. It's also one of the largest such museums still in operation. It's a must-visit, especially if you want to see life-sized dinosaur casts. As a world-class museum, the Field Museum boasts extensive fossil collections. Aside from dinosaur bones, it also displays birds, butterflies, fish, and mollusks. It also has immersive exhibits of ancient cultures, such as those from Egypt and China. There are many other things to see here, considering it holds nearly 30 million objects.

Challenge Your Brain at an Escape Room

Another fun thing to do while you're in Chicago is play at one of its escape rooms. These puzzle games are a perfect brain workout and teamplay for groups and families. You can browse escape rooms here that are just 10 minutes away from the Field Museum by car.

Hotel Sofitel Chicago Water Tower

See the City From Above in Chicago

After your escape room adventure and for more fun activities Chicago, visit the 3,300-foot-long Navy Pier. It's on the Lake Michigan shoreline and home to the Centennial Wheel. This Ferris Wheel affords majestic views of Windy City nearly 200 feet above the ground. The Wheel has a VIP option, giving you a spot at a plush-seated gondola with a glass bottom. Weekend in Chicago

The pier also has other rides like the Light Tower, Wave Swinger, and Tea Cups. If you couldn't do an architectural cruise the day before, get one from the pier. It also offers speedboat tours. If your canine pal is vacationing with you, there's a cruise that both of you can enjoy.

Navy Pier is also home to the Chicago Children's Museum. It offers numerous educational programs best for children ten years and under which is top for fun activities in Chicago. So if you're with your kids, don't miss this, and let them enjoy digging for dinosaur bones. Another attraction at the pier is the award-winning Chicago Shakespeare Theater. It hosts over 650 performances yearly. Check out their official website to time your visit and catch a play or musical here.

Best Things to Do in Chicago

And there you have it, your ultimate guide on how to spend a weekend in Chicago and a guide to activities in Chicago. You may only be in town for two days, but with enough preparation, you can make the most out of it. So, follow our itinerary tips and tricks to have a blast during your 2-day holiday in Windy City. We hope this Best Things to Do in Chicago post inspires you. Happy travels!

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