New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

4-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe. This popular spot is known for its mouth-watering pancakes and other breakfast delights. After fueling up, head over to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (also known as "The Bean") and offers beautiful gardens and art installations.

Afternoon

For lunch, make your way to The Purple Pig, a highly-rated restaurant known for its Mediterranean-inspired small plates. After lunch, take a leisurely stroll along the Chicago Riverwalk. This scenic walkway along the Chicago River offers stunning views of the city's architecture and is perfect for a relaxing afternoon.

Evening

In the evening, enjoy dinner at Giordano's, famous for its deep-dish pizza. After dinner, catch a show at the historic Chicago Theatre, one of the city's most iconic venues.

Bedtime

Find amazing hotels in Chicago, Illinois, USA.

4.69
Millennium Park
Book Now

4.72
Chicago Riverwalk
Book Now

Cultural Gems and Scenic Views

Morning

Begin your day with breakfast at Lou Malnati's Pizzeria, another renowned spot for deep-dish pizza. Following breakfast, visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend your morning exploring its vast collection of artworks.

Afternoon

For lunch, head to Portillo's Hot Dogs to try some classic Chicago-style hot dogs. Afterward, visit the nearby Field Museum, where you can explore fascinating exhibits on natural history.

Evening

Dine at Alinea, one of Chicago's most acclaimed restaurants offering an unforgettable fine dining experience. End your day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking nighttime views of the city from above.

Bedtime

Find amazing hotels in Chicago, Illinois, USA.

4.61
Art Institute of Chicago
Book Now

4.56
Field Museum
Book Now

Architectural Wonders and Local Flavors

Morning

Start your morning with breakfast at The Signature Room at the 95th®️ , which offers stunning views from atop the John Hancock Center. Then head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for more panoramic views of the city.

Afternoon

Enjoy lunch at Frontera Grill, known for its delicious Mexican cuisine by celebrity chef Rick Bayless. Afterward, take an architectural boat tour along the Chicago River to learn about Chicago's rich architectural history.

Evening

Have dinner at Girl & the Goat, a trendy restaurant offering innovative dishes by Chef Stephanie Izard. Conclude your evening with live music at House of Blues, a vibrant venue showcasing top musical acts.

Bedtime

Find amazing hotels in Chicago, Illinois, USA.

4.17
360 Chicago Observation Deck (Formerly John Hancock Observatory)
Book Now

4.61
Chicago River
Book Now

Parks Museums and Culinary Delights

Morning

Kick off your day with breakfast at Eataly Chicago , an Italian marketplace featuring cafes and restaurants. Then visit Museum of Science and Industry, where you can spend hours exploring interactive exhibits.

Afternoon

For lunch, stop by Shaw's Crab House for some fresh seafood delights. In the afternoon, relax in nature by visiting Lincoln Park & Zoo. This expansive park features beautiful gardens and a free zoo that’s perfect for an afternoon stroll.

Evening

End your trip with dinner at Bavette's Bar & Boeuf, known for its steaks and elegant ambiance. Wrap up your night with cocktails at Three Dots and a Dash , a tiki bar offering creative drinks in a fun atmosphere.

Bedtime

Find amazing hotels in Chicago, Illinois, USA.