Weekend in Chicago: Ultimate Things To Do in the Windy City

Ah, the Windy City. Chicago is a sprawling metropolis known for its vibrant social life, impressive architectural feats, tasty local food, and fun city vibe. If you’re headed to the midwest this weekend, you’re in for a real treat. Chicago is brimming with intriguing cultural attractions, fun activities, and countless restaurants and bars to keep you entertained.

There are tons of incredible locations to visit in North America. Still, Chicago shoots to the top of that list as one of the most exciting and diverse American cities to travel to.

Our friends at Hotels.com asked us to share some inspiration on how to spend a weekend in Chicago, and we were happy to oblige.


Visit Chicago This Weekend

Are you looking for things to do this weekend in Chicago? Before you embark on your journey, you may want to make a bucket list of the best places to go in Chicago. Having a bucket list also helps you work out the best spot in town to book a hotel, as you can base your Chicago accommodation around your activities. And lucky for you, we’ve got you covered with a full weekend itinerary to keep you busy while you’re in town.

Keep reading to discover the quintessential Chicago spots you should check out on your vacation.


Chicago Riverwalk

If you’re looking for free things to do in Chicago this weekend, Chicago’s Riverwalk is a classic tourist attraction and a must-see on your first visit to the city. This iconic 1.25-mile stretch passes along the south bank of the Chicago River and ends up in the heart of downtown. This would be a lovely spot to take a stroll on a sunny Sunday in Chicago.


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There are countless waterfront restaurants and cafes for you to stop at along the way, where you can sip on a cup of coffee as you watch the locals enjoy the waterway. You’ll see kayakers, pedestrians, cruise liners on the water, and plenty of activity on this strip. The Riverwalk is also an excellent spot to marvel at Chicago’s famous architecture. The soaring buildings look majestic from the waterway.

If you want to learn more about iconic architecture, you can take the Chicago River Guided Architecture Cruise. This luxurious cruise will take you on an unforgettable boat ride along the river, and teach you some essential information about Chicago’s architectural scene.


Millennium Park

Nestled in the Loop area of Chicago, Millennium Park is a stunning public park boasting over 300 acres of land. The park isn’t just a great place to take a stroll or lay out a picnic. You can also find art sculptures on the grounds, such as The Crown Fountain. It’s an interactive art piece and video sculpture standing 50 feet tall that you’ve got to check out.


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Millennium Park is also home to the Cloud Gate sculpture, or “The Bean,” as locals call it. This odd artwork shaped like a legume is featured in countless Hollywood features set in Chicago. And you can see this iconic three-story steel sculpture for yourself during your Chicago adventure.


Gogh with Lifeway Immersive Yoga at Lighthouse ArtSpace

How many people can say they’ve done a yoga session to the backdrop of a Van Gogh exhibition? Gogh with Lifeway offers one of the most unique, rewarding, and rejuvenating experiences in the city. If you’re one of the millions of yoga enthusiasts out there who are chasing serenity, you will fall in love with this immersive yoga experience.

Head to the Lighthouse ArtSpace for this magical exhibition. Take a deep breath and find your zen while projections of Van Gogh’s mesmerizing artworks play out all around you. This is a top-notch experience in Chicago not to be missed.


Lincoln Park

Lincoln Park is a beautiful park on Chicago’s north side and the biggest in the city. You’ll see lovely manicured lawns, botanical gardens, and a gorgeous lake here, not to mention the city skyline in the background.

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If you’re visiting Chicago in the spring, a trip to the Lincoln Park Conservatory is a must. The Conservatory holds a Spring Flower Show displaying rows on rows of azaleas, hydrangeas, tulips, and much, much more.

Enter the magnificent Victorian greenhouse, marvel at the hundreds of flowers in bloom, and take in a beautiful spring day at this magical Chicago spot.


Willis Tower Skydeck

Situated in the heart of downtown Chicago, Willis Tower is an impressive skyscraper standing over 100 stories tall. You can’t miss this building from the outside, but trust us, the view from the inside is nothing in comparison.

The Willis Tower Skydeck is an observation point that sees over a million visitors every year. Once you see the Chicago skyline from 1,353 feet in the air, you’ll never forget your vacation to this fantastic city.


Art Institute of Chicago

The Art Institute of Chicago is an esteemed art museum in the Grant Park neighborhood and an excellent spot if you’re looking for fun things to do in Chicago’s suburbs. The Institute is home to an impressive collection of fine art and curated exhibitions, and you can see world-famous pieces there, too. One noteworthy artwork to check out is Edward Hopper’s famous Nighthawks painting from 1942. If you want to skip the queues at this popular museum, you can buy a fast pass online ahead of time.


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You can also spot renowned works such as The Bedroom by Van Gogh, Grant Wood’s American Gothic, and Claude Monet’s Water Lilies. If you’re looking for a fantastic display of Chicago’s arts and culture scene, this is the spot for you. With over 300, 000 artworks and an extensive selection of impressionist art, you’ll be occupied for hours at this fine establishment.


Magnificent Mile

Chicago’s main commercial district, Magnificent Mile, or Mag Mile, is a buzzing area filled with high-end boutiques, fancy restaurants and bars, and upscale hotels. You’ll also see iconic landmarks at Mag Mile, such as the Chicago Water Tower, the Wrigley Building, and the City Gallery.


Enjoy Your Chicago Weekend Getaway

No matter where you are in Chicago, there is always something intriguing to see. Whether you’re dining out by the river, taking a stroll through Lincoln Park, or admiring city views from Willis Tower, you’ll have a blast exploring the epic Windy City.


Chicago weekend getaway


If you’re looking for some more fun travel inspiration for your next adventure, you can read up on the breathtaking Yellowstone Park. This is another fantastic location to take a road trip to if you’re up for an exciting weekend getaway.

The U.S is abundant with travel spots any tourist would love, and we’ve got you covered with all the information you need for your dream trip. Enjoy your Chicago vacation!


COVID Travel Advisory

As travel continues to open please be mindful that travel regulations and guidelines can always change. It’s important to take care of your safety and the safety of others when planning and going on a trip.

To prepare yourself for travel please take into account these tips:

  • Wear a face mask whenever required by local and state laws. It’s always good to have a few extra to make sure you’re never without.
  • Carry hand sanitizer with you at all times, including a few extras in all the different travel bags you have.
  • Do you research on the destinations that you’re traveling to and be sure to recheck just before you leave on your trip. Check local websites, Twitter, Facebook, etc, to get real time information of closures, restrictions and regulations in place.
  • Research and book a hotel that offers free cancellation in case you need to change your plans at the last minute.

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