Things To Do
Millennium Park
Millennium Park is one of Chicago’s most iconic attractions, located right in the heart of downtown. Known for its striking public art and green spaces, it’s home to the famous reflective sculpture nicknamed “The Bean” (officially Cloud Gate.) Visit early in the morning or later in the evening if you’d like photos at The Bean without heavy crowds. The park connects directly to the Art Institute of Chicago and Maggie Daley Park, making it easy to explore multiple attractions in one outing.
Chicago Lakefront Trail
The Chicago Lakefront Trail is an 18-mile paved path that runs along Lake Michigan, connecting many of the city’s beaches, parks, and neighborhoods. Perfect for walking, jogging, or biking, the trail offers beautiful views of both the lake and the skyline. Bike rentals: Divvy, Chicago’s bike-share program, has stations all along the trail and is an easy way to explore. Best views: The stretch between Museum Campus and Oak Street Beach offers some of the most iconic skyline and lake views.
The Art Institute of Chicago
The Art Institute of Chicago is one of the world’s great art museums, located in the heart of downtown. Its collection spans thousands of years and includes everything from ancient artifacts to modern masterpieces. Highlights include Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and works by Monet, Van Gogh, and Picasso. The building itself, with its iconic bronze lion statues at the entrance, is a Chicago landmark. General admission tickets are $32.
Riverwalk
The Chicago Riverwalk is a vibrant pedestrian path along the south bank of the Chicago River in downtown. It’s the perfect place for a walk, people-watching, or simply enjoying stunning views of the city’s architecture and bridges. Stop at 'Tiny Tapp' or 'City Winery' for casual bites and drinks. Consider a boat tour or kayak rental right off the Riverwalk to see the city from the water.
Chicago Magic Lounge
Chicago Magic Lounge is a one-of-a-kind venue dedicated to the city’s rich history of close-up magic. Tucked behind a laundromat entrance, the theater combines speakeasy vibes with incredible performances, from sleight-of-hand at the bar to full-scale stage shows. It’s a uniquely Chicago experience that blends mystery, comedy, and plenty of surprises. Tickets often sell out in advance. Arrive before the main show to enjoy table-side magic in the lounge and cocktails with whimsical twists. The hidden entrance (through a faux laundromat) is part of the fun!
Lincoln Park Zoo
Lincoln Park Zoo is one of the few major zoos in the country that is completely FREE to visit. Located just north of downtown, the zoo is home to hundreds of animals and offers beautiful grounds to explore, making it a perfect outing anyone who loves animals and nature. Beyond the animal exhibits, the surrounding area is just as lovely. Take a walk around North Pond for peaceful views of the skyline reflected in the water. The zoo is open every day of the year, and admission is always free.
The Green Mill
The Green Mill is a legendary jazz club in Uptown. Open since 1907, it’s one of Chicago’s most historic music venues. It’s best known for its incredible live jazz, vintage atmosphere, and classic Chicago character. The club is cash-only, and there typically is a cover charge to get in. They do not take reservations, and often fill up quickly. Arrive early if you want a good seat.
River Cruise Architecture Tour
Often considered a must-do in Chicago, this 90-minute boat tour aboard Chicago’s First Lady gives you a front-row seat to the city’s world-famous architecture. Guided by expert docents from the Chicago Architecture Center, the cruise takes you along the Chicago River with fascinating stories behind the skyline’s history, design, and iconic buildings. Tickets sell out quickly, especially on weekends, so we recommend booking in advance through the Chicago Architecture Center. Ticket pricing is approximately $50.
Griffin Museum of Science and Industry
The Museum of Science and Industry is one of the largest science museums in the world, packed with interactive exhibits that bring science, technology, and history to life. Highlights include a real German World War II submarine (the U-505), a massive model railroad, a replica coal mine, and a rotating lineup of hands-on exhibits. The museum itself is housed in a stunning building from the 1893 World’s Fair, adding to its historic charm. General admission tickets are $25. The museum is located in Hyde Park, a beautiful South Side neighborhood that’s also home to the University of Chicago and lovely parks along the lakefront.
The 606
The 606, also known as the Bloomingdale Trail, is an elevated 2.7-mile walking and biking path built on a former rail line. Stretching through Logan Square, Bucktown, Humboldt Park, and Wicker Park, it’s lined with public art, murals, gardens, and scenic overlooks, offering a unique way to explore Chicago’s neighborhoods from above street level. You can hop on at multiple access points. Damen Avenue and Milwaukee Avenue are two of the most convenient for visitors. Pair your stroll with a stop at one of the nearby cafés, breweries, or restaurants in Logan Square or Wicker Park.
Second City Main Stage
The Second City is Chicago’s legendary comedy club, famous for launching the careers of comedians like Tina Fey, Steve Carell, and Bill Murray. With a mix of sketch comedy, improv, and stand-up, it’s the perfect place to experience Chicago’s sense of humor and see future stars in the making. Shows run almost every night. Check the schedule in advance, as weekend performances often sell out. The theater is located in the Old Town neighborhood, surrounded by great bars and restaurants - perfect for dinner and a show The venue has a full bar and offers food during shows.
Field Museum
The Field Museum is Chicago’s world-renowned natural history museum, home to fascinating exhibits that bring science, culture, and history to life. Highlights include SUE the T. rex, the largest and most complete Tyrannosaurus rex fossil ever discovered. The museum is massive, and it’s easy to spend a full day exploring. General admission tickets are $30. The museum is located in Museum Campus alongside the Shedd Aquarium and Adler Planetarium, so it’s easy to pair your visit with another Chicago landmark. Don’t miss the view just outside! The steps of the Field Museum offer one of the best skyline panoramas in the city, stretching across Grant Park to downtown. A great spot for photos!
Goose Island Taproom
Goose Island is Chicago’s most famous craft brewery, credited with helping launch the city’s craft beer scene. A tour of their production brewery gives you a behind-the-scenes look at how their beers are made, from brewing to bottling, along with plenty of samples of their classic and seasonal offerings.
Ping Tom Park and Chinatown
Ping Tom Memorial Park is a beautiful riverfront park in Chicago’s Chinatown, offering skyline views, gardens, and plenty of space to relax. Just steps away is Chinatown, where you’ll find vibrant shops, bakeries, and some of the city’s best Chinese restaurants. It’s a wonderful spot to combine a peaceful walk by the river with exploring a lively cultural neighborhood. This park is extra special to us! Ping Tom Park was where we had our very first date, and it’s also where Ramiro proposed!
360 CHICAGO
Located on the 94th floor of the former John Hancock Center, 360 Chicago offers sweeping views of the city, Lake Michigan, and even neighboring states on a clear day. It’s also home to Tilt, a thrill ride that tilts visitors out over Michigan Avenue for a one-of-a-kind perspective. General admission tickets are $29. Chicago also has the Willis Tower, known for its glass “Ledge” where you can step out over the city. Personally, we think 360 Chicago offers the better skyline view and tends to be less crowded.
The iO Theater
iO Theater is one of Chicago’s top spots for improv comedy, known for its innovative shows and talented performers. One of the standout productions, and one of our FAVORITES, is Improvised Shakespeare, where actors create a completely new play on the spot in the style of Shakespeare complete with rhymes, monologues, and plenty of laughs. It’s a truly unique Chicago theater experience that blends wit, creativity, and comedy. Improvised Shakespeare is a fan favorite and often sells out. We recommend that you buy tickets in advance if this is on your list
Garfield Park Conservatory
Often called “landscape art under glass,” the Garfield Park Conservatory is one of the largest and most beautiful botanical conservatories in the country. With lush indoor gardens, dramatic palm houses, and vibrant seasonal flower displays. Reservations are required to enter. Advance reservations are strongly recommended. Admission is technically free, with a suggested $10 donation.
Wrigley Field
Wrigley Field, home of the Chicago Cubs, is one of the most iconic ballparks in the country. Even if you’re not a big baseball fan, it’s worth a visit for the history, classic ballpark atmosphere, and lively neighborhood vibe that surrounds it. If you can’t make a game, the Wrigley Field Tours offer behind-the-scenes access, including the dugout, press box, and field.
Chicago Cultural Center
The Chicago Cultural Center is a stunning architectural gem located across from Millennium Park. Once the city’s main public library, the building is now a free arts and cultural space hosting rotating exhibits, performances, and events. It’s most famous for its two breathtaking stained-glass domes, including the world’s largest Tiffany dome. Admission is FREE. The Cultural Center is directly across from Millennium Park, so it pairs perfectly with a visit to The Bean and the Art Institute.
Royal Palms Shuffleboard Club
Royal Palms is a playful bar in Chicago’s Wicker Park neighborhood where guests can sip tropical-inspired cocktails and try their hand at shuffleboard. The space has a laid-back, retro feel with bright décor, lively music, and a rotating lineup of local food trucks, making it a great spot to hang out! Courts are first-come, first-served, but you can also reserve ahead online to guarantee play time. Don’t worry if you’ve never played shuffleboard. The staff is happy to teach you the rules. Grab drinks at the full bar and enjoy bites from the rotating lineup of local food trucks parked inside.
Andersonville
This neighborhood is extra special to us - it’s where we live! Andersonville is one of Chicago’s most charming neighborhoods, known for its historic Swedish roots, welcoming community, and eclectic mix of shops, restaurants, and cafés. It has a laid-back, neighborhood feel while still being full of things to explore. Walk down Clark Street to discover unique boutiques, vintage shops, and local gems. Favorite spots include Hopleaf (a Belgian-inspired pub with an incredible beer list), Little Bad Wolf (one of the best burgers in the city), and M. Henry (a cozy brunch spot). For shopping, check out Andersonville Galleria, a multi-level space featuring local artists and makers. Green thumbs will love Gethsemane Garden Center, a beloved neighborhood staple filled with plants, garden décor, and inspiration. Stop by Eli Tea Bar for bubble teas, tea lattes, and a cozy spot to unwind.