New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

4-Day Chicago Adventure

4-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning
Start your Chicago adventure with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (The Bean) and offers beautiful gardens and public art installations. Enjoy a morning stroll and take some memorable photos.
Afternoon
Head over to The Magnificent Mile for some afternoon shopping and sightseeing. This bustling avenue is lined with high-end shops, restaurants, and historic landmarks. Don't forget to stop by Giordano's for a classic Chicago deep-dish pizza lunch.
Evening
End your day with an evening at House of Blues. Enjoy live music in this legendary venue that features a mix of genres from blues to rock. For dinner, indulge in some delicious Southern-inspired cuisine at the House of Blues restaurant.
Bedtime
Find amazing hotels in Chicago, Illinois.

Exploring Chicago's Cultural Gems

Morning
Begin your day with a visit to the Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from around the globe. Spend your morning exploring its impressive exhibits.
Afternoon
After soaking in the art, take a short walk to Grant Park for a relaxing afternoon amidst beautiful greenery and fountains. For lunch, head over to The Purple Pig nearby for some Mediterranean-inspired small plates.
Evening
In the evening, make your way to Chicago Theatre. Catch a show or simply admire the stunning architecture of this historic venue. For dinner, dine at Au Cheval, known for its mouthwatering burgers.
Bedtime
Find amazing hotels in Chicago, Illinois.

Architectural Wonders and River Views

Morning
Kick off your day with an architectural tour along the Chicago Riverwalk. Learn about Chicago's iconic buildings while enjoying scenic views of the river.
Afternoon
Continue your exploration with a visit to the historic Rookery Building, one of Chicago's architectural masterpieces designed by Frank Lloyd Wright. Have lunch at Girl & the Goat, offering innovative dishes in a trendy setting.
Evening
Spend your evening at Navy Pier (not on wishlist), where you can enjoy rides, games, and stunning views of Lake Michigan. For dinner, savor fresh seafood at Joe's Seafood, Prime Steak & Stone Crab.
Bedtime
Find amazing hotels in Chicago, Illinois.

Sports and Skyline Views

Morning
Start your day with a visit to Wrigley Field, one of baseball's most iconic stadiums. Take a guided tour or catch a game if there's one scheduled.
Afternoon
Head over to Lincoln Park & Zoo (not on wishlist) for an afternoon surrounded by nature and wildlife. It's perfect for families or anyone looking for a peaceful escape within the city. Grab lunch at nearby Lou Malnati's Pizzeria for another taste of deep-dish pizza.
Evening
Conclude your day with breathtaking views from the 360 Chicago Observation Deck (not on wishlist). Watch as the city lights up below you from this sky-high vantage point. For dinner, enjoy Italian cuisine at RPM Italian.
Bedtime
Find amazing hotels in Chicago, Illinois.

Science and Industry Extravaganza

Morning
Begin your day with a visit to the Museum of Science and Industry. This massive museum offers interactive exhibits and fascinating displays on everything from space exploration to genetics. Plan to spend a few hours here as there's plenty to see and do.
Afternoon
After an engaging morning, head over to Shedd Aquarium for an afternoon with marine life. This renowned aquarium features a wide variety of aquatic creatures and immersive exhibits. For lunch, enjoy some delicious BBQ at Smoque BBQ, located nearby.
Evening
Wrap up your Chicago adventure with a relaxing evening at the Chicago River. Take a sunset cruise or simply stroll along the riverwalk, soaking in the beautiful cityscape. For dinner, treat yourself to an exquisite meal at Alinea, one of Chicago's most acclaimed restaurants.
Bedtime
Find amazing hotels in Chicago, Illinois.
kayakFind the right stay during your trip.
Got a question about your trip?