Chicago: Rivers to Rooftops
- May 4
- 6 min read
Chicago offers a unique blend of unexpected art, delicious food, and lively rooftop scenes. This 3-day itinerary takes you through some of the city’s quirkiest art spots, tasty local eats, and rooftop hangouts where the energy is contagious. Whether you’re a first-time visitor or a returning explorer, this plan balances culture, adventure, and relaxation with a touch of Chicago’s signature charm.
Day 1:
Kick off your Chicago adventure with a fun brunch to set the mood! Swing by El Mariachi for their $20 bottomless mimosas brunch on Fridays, Saturdays, and Sundays. You get unlimited mimosas for 2 hours when you grab an entrée. Just a heads up, it gets busy, so don't wait too long!
After brunch, take a quick ten-minute stroll to the Lakefront Trail, an 18 to 19-mile paved path along the Lake Michigan shoreline, linking up parks, beaches, and neighborhoods. It's a top spot for walking, running, and biking, with amazing views of the city skyline and the lake.
Next, hit the water and try Kayaking along the Chicago River. It's a cool way to check out the city's architecture and urban vibe from a fresh perspective for just $63. Once you launch, it's a quick paddle south to the main east/west branch of the river. Enjoy a kayak trip through the stunning skyscraper canyon and along the riverfront path. You can make it from the launch point to almost the entrance of Lake Michigan and back in about 1.5 hours.
After building up an appetite, head over to Tacotlan, a cherished local gem renowned for its outstanding and genuine Mexican flavors. Just a quick 21-minute drive will bring you to this lively taco spot, where you'll find a mouthwatering selection of choices that thrill both traditionalists and adventurous foodies alike!
In the evening, swing by Art on the MART, an awesome digital art show on the Merchandise Mart building. It's just a 25-minute drive and a fun way to catch some public art in Chicago.
Finish off your day at PANCHOS ROOFTOP, just a quick 10-minute jaunt away. This buzzing rooftop bar in Chicago's South Loop is the perfect spot to unwind. Don’t miss out on the soft serve margaritas—they’re like dessert, but with a kick.
Day 2:
Start day two with enthusiasm at the Museum of Science and Industry and plunge into the Blue Paradox exhibit! This spectacular display features floor-to-ceiling screens that envelop you in an LED Wave Wall of stunning ocean imagery, from vibrant coral reefs to captivating swarms of jellyfish. For just $26, your general admission unlocks access to most of the permanent exhibits and some extraordinary temporary exhibitions. Prepare for an unforgettable adventure!
For lunch, head south 10 minutes to Ricobene’s, a legendary, family-owned Chicago institution that has been serving Italian-American comfort food since 1946. It is world-renowned for its signature Breaded Steak Sandwich, which was famously named the "Best Sandwich in the World" by USA Today.
Get ready for an afternoon full of creativity at Spin Art Nation, where you'll embark on an unforgettable hands-on adventure! It's just a 30-minute drive from lunch and only $6 per painter, per hour for studio time, plus whatever your canvas and art pieces end up costing. At Splatter Studio, you'll jump into a high-energy, glow-in-the-dark paint party where you can fling, splash, and spray paint to create bold, expressive masterpieces.
After a day of crafting, indulge in an unforgettable escape at Aire Ancient Baths River West, just a quick 20-minute drive away! Make sure to book at least two weeks in advance and dive into a sensory journey within a beautifully restored historic building, illuminated by the soft glow of candles. For just $175, embark on a self-paced tour through thermal baths of varying temperatures. Enjoy 90 minutes of pure bliss with our thermal tour, featuring:
Caldarium (Hot Bath)
Frigidarium (Cold Bath)
Tepidarium (Warm Bath)
Balneum (Bath of Thousand Jets)
Vaporium (Two Steam Rooms with Aromatherapy)
Palestra (Indoor/Outdoor Bath)
Flotarium (Salt Bath)
Just 20 minutes up the road, dive into the unlimited hot pot experience at Happy Lamb in Chinatown! It's the perfect way to warm up and enjoy a meal with friends. Your gateway to the finest inner-Mongolian-style hot pot adventure awaits. Immerse yourself in a culinary journey where our rich broths, premium meats, and lively atmosphere will excite and delight all your senses!
Wrap up your night with some live tunes at Schubas Tavern. It's just a quick ten-minute drive to this cozy spot that's famous for awesome concerts. Ticket prices change depending on who's playing, but there's always something happening, making it the ideal place to relax with some drinks and good entertainment.
Day 3:
Get ready for an exciting final day packed with culture! Kick off with a visit to the Chicago Cultural Center, where you'll be wowed by its breathtaking architecture and dynamic rotating exhibits. While there are countless exhibits to explore, the true masterpiece is the building itself. Don't miss the chance to marvel at the intricate staircases and ceilings, especially the awe-inspiring glass dome!
Right across the street, you can't miss the famous Cloud Gate, also known as the Chicago Bean. It's a must-see symbol of the city and a top spot for tourists. The sculpture, inspired by liquid mercury, has a shiny, seamless stainless steel surface that reflects and twists the Chicago skyline and the nearby park.
Embark on a delightful 15-minute walk to The Rookery, a historic gem boasting an extraordinary interior crafted by the legendary Frank Lloyd Wright. Don’t miss out—book your Guided Tour for just $20 today! During this captivating tour, you'll explore the stunning Wright-designed Rookery lobby and the fascinating Burnham Library. Join us on Mondays and Wednesdays for an unforgettable one-hour experience!
Just a 10-minute walk away, you'll find the Winter Garden at Harold Washington Library. It's a gorgeous spot on the 9th floor, full of plants and bathed in natural light. This beautiful, sunny atrium is perfect for some quiet time, whether you're reading, studying, or just kicking back and relaxing.
When your stomach starts sounding like a marching band, we can scoot north 10 minutes and grab lunch at the legendary Billy Goat Tavern. This place serves up a slice of Chicago’s dining history without any fancy frills. It's a historic landmark famous for its "Cheezborger" and its starring role in local sports and pop culture shenanigans. Founded way back in 1934, it shot to fame thanks to a hilarious Saturday Night Live sketch and the infamous "Curse of the Billy Goat".
After lunch, let's zoom over to The Color Factory Chicago—just an 8-minute drive away! For only $29, you can dive into a world of vibrant wonder with 14 immersive art exhibits that are as breathtaking as they are colorful. Get excited for an adventure filled with surprise giveaways, delightful sweet treats, and free digital photos to capture every unforgettable moment of your experience!
Head uptown for just 10 minutes and hop on an exciting Water taxi to Chinatown! These fantastic water taxis operate from May through October, offering an unforgettable ride for about $10 each way. They connect several Chicago neighborhoods with a plethora of dining, sightseeing, and shopping attractions!
You'll get dropped off right In Chinatown, stroll through Ping Tom Memorial Park, a peaceful riverside spot. Often described as a "hidden gem," it features a distinctive pagoda-style pavilion, bamboo gardens, and some of the best views of the Chicago skyline.
For a hilarious happy hour, get ready for a quick 25-minute trip to Zanies Comedy Club. This comedy spot has an awesome lineup of comedians and is the perfect way to end your trip with some serious laughs. Located in the Old Town neighborhood of Chicago, this iconic comedy club is the city's original stand-up comedy venue. Since 1978, it’s been delivering laughs with a cozy, "old school" feel, showcasing a mix of local talent and famous comedians.
If you're still feeling hungry, hop in the car for a quick 15-minute drive to the Golden House Restaurant for some late-night snacks. When you get there, don't worry if it doesn't look like much at first. Once you order, you'll get it. Fun fact: it was also used as the filming spot for Patsy’s Pies in the Showtime series Shameless.
Tips for a Smooth Trip
If the Balloon Museum is still in town, you absolutely must visit for an unforgettable, quirky, family-friendly adventure! Art that you can touch, experience, and share—never static—fosters an exciting and innovative connection with the viewer. The four incredible exhibitions, Pop Air, Let’s Fly, EmotionAir, and Euphoria, are the thrilling outcome of a process that has been both rapid and extraordinary.
Reserve El Mariachi brunch early to secure bottomless mimosas and keep in mind the 90-minute limit.
Book Aire Ancient Baths at least two weeks ahead; it’s a quiet, adult-only space.
The Balloon Museum is a pop-up exhibit; check dates before planning your visit.
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