Looking for the perfect way to spend a weekend in Chicago? Whether you’re visiting for the first time or looking for inspiration on things to do, this guide has everything you need to make the most of your trip in the Windy City. From iconic landmarks to hidden gems, Chicago is full of culture, history, and yummy eats.
Having lived in Chicago for two years during business school, I spent many weekends exploring the city and curating a go-to itinerary for whenever friends came to visit. Lucky for you, I’m sharing it all in this blog post! In this guide, I’ll show you how to experience the best of Chicago in just one weekend, with a bucket list that balances must-see attractions, local favorites, and plenty of time to relax and enjoy the city’s fun energy.
When is the best time to visit Chicago?
In my opinion, the best time to visit Chicago is between the months of April and October. Winter in Chicago can be brutally cold and feel like it lasts longer than it actually is. In April, the weather starts to warm up a bit and the flowers are in full blossom. Springtime in Chicago is beautiful, but summer can’t be beat. With the calm blue waters of Lake Michigan and the warm sunshine, you’ll find all the locals outside and the city really coming to life. Come fall, Chicago offers the perfect blend of crisp air and vibrant autumn colors. As the city transforms with shades of red, orange, and gold, it’s a prime time to explore Chicago’s many outdoor and indoor attractions as temperatures get cooler.
Top 10 Things To Do in Chicago
Keep on reading for the best things to do in Chicago for a fun and memorable weekend getaway!
1. Visit Chicago’s Iconic Landmarks
Chicago is renowned for its architecture, so you can’t visit without checking out some of its most iconic landmarks! Head over to Millennium Park to snap an obligatory photo at the Bean, then cross the street to see the stunning Tiffany dome at the Chicago Cultural Center. Just a short walk away is the Wrigley Building, one of my favorite buildings in the city.
2. Explore the Galleries at the Art Institute
The Art Institute of Chicago boasts an impressive collection of works — from ancient artifacts to contemporary masterpieces, there’s something for every art lover. My favorite exhibits are the Impressionist Wing on the second level (love me some Monet!) and the Thorne Miniature Rooms on the lower level. It’s unbelievable how real the miniature rooms look — I especially loved the French provincial and British countryside replicas. It felt straight out of Bridgerton!
3. Take a Stroll Along the Riverwalk
One of my favorite activities in Chicago is taking a scenic stroll along the Riverwalk. This peaceful path offers stunning views of the city’s iconic landmarks and many bridges. You can stop for a coffee or a bite at one of the many riverside cafes or even rent a kayak to paddle along the water. It’s the perfect spot to relax and people-watch while enjoying the vibrant atmosphere of the city. When the weather is warm, I love to curl up here with a book.
4. Go on an Architecture Boat Tour
One of the best ways to experience Chicago’s architecture is by taking an Architecture Boat Tour along the river. Hear about the history of Chicago’s architectural evolution and the iconic buildings that define its skyline. I’ve done it multiple times myself, both as a tourist and with friends, and I learn something new every time!
5. Hang Out with the Animals at Lincoln Park Zoo or Shedd Aquarium
For a family-friendly or nature-filled experience, Chicago is home to two top-notch attractions where you can spend time with animals. Lincoln Park Zoo, located in the heart of the city, is one of the oldest zoos in the country — and best of all, admission is free! During the winter holidays the zoo transforms into a winter wonderland with its Zoolights festival, an absolutely must-see. Alternatively, head to Shedd Aquarium, where you can see everything from playful dolphins to majestic beluga whales. The sea otters are adorable and stole my heart!
6. See the Skyline From North Avenue Beach or Milton Lee Olive Park
For panoramic views of Chicago’s skyline, head to North Avenue Beach or Milton Lee Olive Park. North Avenue Beach is a popular spot for bike rides, beach volleyball, and scenic walks along the shore of Lake Michigan. If you prefer a quieter spot, Milton Lee Olive Park is great for a relaxing picnic or a sunset stroll.
7. Watch a Sports Game at Wrigley Field or the United Center
Chicago is home to passionate sports fans, and no trip would be complete without taking in a game at one of its legendary sports venues. Check out Wrigley Field, home to the Chicago Cubs, for a baseball game or head over to the United Center to catch the Chicago Bulls play an NBA match. The energy level is unmatched!
8. See a Show at The Second City or the Green Mill Jazz Club
Chicago has a rich history of entertainment and nightlife, and there’s no better place to experience it than at the Second City or The Green Mill. The Second City is an icon in the improv scene, launching the careers of many famous comedians including Tina Fey, Amy Poehler, and Steve Carell. For a more laid-back evening, head to the Green Mill jazz club for some live performances in an intimate setting.
9. Walk the 606
If you enjoy exploring unique urban spaces, don’t miss a walk along the 606 — an elevated, 2.7-mile-long trail that runs through several neighborhoods, offering a calm escape from the hustle and bustle of the city. The 606 is perfect for walking, jogging, or cycling and is a great way to explore some of Chicago’s hip neighborhoods, such as Wicker Park and Logan Square. Along the way, you’ll pass through parks, art installations, and colorful street murals. Be sure to stop by Ipsento 606 for delicious coffee and treats.
10. Take a Trip Up to the Baháʼí House of Worship
If time permits, I highly recommend driving or taking the train up to the Baháʼí House of Worship. Known for its unique shape and serene gardens, this house of worship offers visitors a peaceful escape from the city and is well worth the trip. The building is open to the public, and its stunning design and beautiful landscaping make it an ideal spot for reflection and contemplation. It’s especially beautiful in the spring when the magnolia trees are in full bloom.
My Favorite Chicago Restaurants
Of course, how can I create a Chicago guide without including some of my favorite eats? Chicago has a diverse food scene and I have yet to make my way down my (very long) food bucket list, but over my two years of living there, there are a few places I can’t stop thinking about.
For a delicious breakfast check out Kasama, a Michelin starred bakery, café, and modern Filipino tasting menu that was featured on The Bear. Lines form around the block before they even open, so I recommend getting there early (preferably on a weekday) to cut your waiting time. To give you a rough idea, a friend and I went on a Sunday morning right before opening and waited over 2 hours in the cold to grab some pastries and drinks to-go. It was freezing and I was very hangry, but this was high on her bucket list and she was visiting town for the first time, so we had to do it! But when I went again with a group of classmates on a Wednesday, we only waited 15 minutes before we were seated at a table.
For lunch, one of my most memorable meals was at Monteverde. This place is a bit pricier but absolutely delicious and worth it, as the chef won a James Beard award. Their burrata appetizer is heavenly, along with their unique pastas made from seasonal and local ingredients. I love coming here with friends and sharing multiple items so that we can try them all.
Spacca Napoli is also a great place to grab a bite, and the only way to place a reservation is by phone. Otherwise, expect a wait during evenings and peak times. Their pistachio pizza lives rent free in my head and I keep dreaming about it!
For dinner, I love Beatnik on the River for their beautiful vibes and delicious food. I celebrated my birthday here with a group of friends and it was a really special night. If you can, try to get a table on the terrace for a view of the riverfront.
Lastly, as an afternoon tea enthusiast, The Drake Hotel is the perfect place to relax or celebrate with friends. During the holidays, they have a special holiday tea service in the Palm Court, where you can get serenaded by carolers. A group of friends threw a little send-off here for me before I moved to London for my exchange, and it was so cute and aesthetic!
Other restaurants on my bucket list that have been highly recommended by friends:
- Au Cheval
- HaiSous
- ROOH
- Ema
- Aba
- Tortello
- Avec
- Akahoshi Ramen
- Daisies
- Qing Xiang Yuan Dumplings
- Alla Vita
- Ramen Wasabi
- Cafe Ba-Ba-Reeba
- Siena Tavern
Conclusion
No matter what kind of traveler you are, Chicago offers something for everyone. With this guide, I hope you’ll be able to experience the most that this city has to offer. Ready for an adventure in the Windy City? Start planning your trip today and get ready for a fun time!
