Things To Do

Architecture Tour

One of the best ways to see Chicago is from the water. The city is home to two stunning waterfronts, the Chicago River and Lake Michigan, with each offering plenty of cruise options. Admire the skyline on a lakefront cruise or do one of Justin's favorite activities and learn about the city’s iconic architecture on a Chicago River cruise.

Cubs Game at Wrigley Field

The Cubs will be in town this week, hosting the St. Louis Cardinals. Thursday: 7:05pm Friday: 1:20pm Saturday 1:20pm (Wedding Day, don't go to the game this day) Sunday 1:20pm

Chicago Riverwalk

Located on the south bank of the Chicago River, the award-winning, pedestrian-friendly Chicago Riverwalk stretches 1.25 miles from Lake Michigan to Lake Street. Along the way you’ll discover intimate coves, breezy cafes, wineries and bars, public art, monuments, museums, and a boatload of excursions on the water.

Lakefront Trail

The Lakefront Trail, a scenic pedestrian pathway that stretches for more than 18 miles, offers stunning views of the lake and city skyline.

Millennium Park

Millennium Park is an award-winning center for art, music and architecture. It’s prominent features are the Frank Gehry designed outdoor concert venue, the interactive Crown Fountain and and the hugely popular Cloud Gate sculpture aka "The Bean"

Museum Campus

Navy Pier

Navy Pier is a 50-acre scenic waterfront destination that’s home to countless restaurants, exhibitions, shops, entertainment, and more. Take a ride on the 200-foot-tall Ferris wheel, explore the interactive Chicago Children’s Museum, enjoy a free concert, or go on an art and mural hunt—all against the spectacular views of Lake Michigan and the Chicago skyline. Adrenaline seekers will love the speedboat tours; otherwise, unwind on a sightseeing cruise.

The Magnificent Mile

The Magnificent Mile is one of the most famous shopping areas in the world — home to a dizzying array of popular stores, restaurants, attractions, and architecture all on one iconic street.

Sears (Willis) Tower

Experience jaw dropping views from Chicago's iconic Sears Tower (Willis) spanning throughout Chicagoland and up to four states!

Oak Street Beach

Chicago is home to miles and miles of sandy shoreline, where you can swim, bike, kayak, boat, jet ski, paddle board, sip cocktails on the waterfront, and more.

Lincoln Park Zoo

Lincoln Park Zoo is free, open every day of the year.

Shedd Aquarium

The Shedd Aquarium is a highly-ranked world aquarium and at one time was the largest indoor facility in the world.

The 606 Trail

What was an abandoned rail line is now The 606. Its 2.7 miles of multi-use recreational trail and park is an alternative transportation corridor, a living work of art, and a spectacular new green space for all to enjoy.

NASCAR Chicago Street Race

The NASCAR Chicago Street Race will take place on July 5-6. Located one block over from the Palmer House hotel in downtown Chicago, the 2025 event will take NASCAR's past and through many of the city’s most renowned downtown landmarks on Michigan Avenue, South Columbus Drive, South DuSable Lake Shore Drive and the start-finish line near Buckingham Fountain.

Musicals and Shows

Chicago is home to award winning musicals and plays. Check out a show while in town.