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 day with a visit to Millennium Park, where you can see the iconic Cloud Gate sculpture and enjoy the beautiful gardens. Grab breakfast at Lou Malnati's Pizzeria, famous for its deep-dish pizza.
Afternoon
Head over to Art Institute of Chicago for an afternoon of exploring world-class art collections. For lunch, try The Purple Pig, known for its Mediterranean-inspired small plates.
Evening
End your day with a visit to Chicago Riverwalk, where you can take a leisurely stroll along the river. Have dinner at Girl & the Goat, a highly-rated restaurant offering innovative dishes.
Bedtime
Find amazing hotels in Chicago, Illinois.

Cultural and Historical Highlights

Morning
Begin your day at Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of its tallest buildings. Enjoy breakfast at Au Cheval, renowned for its delicious brunch options.
Afternoon
Spend your afternoon exploring Field Museum, one of the largest natural history museums in the world. For lunch, head to Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.
Evening
In the evening, visit Chicago Theatre to catch a show or simply admire its historic architecture. Dine at Bavette's Bar & Boeuf for an unforgettable steak dinner.
Bedtime
Find amazing hotels in Chicago, Illinois.

Architectural Wonders and Lakeside Fun

Morning
Kick off your morning with a tour of Marina City, an architectural marvel. Have breakfast at Frontera Grill, known for its gourmet Mexican cuisine.
Afternoon
Spend your afternoon at Navy Pier, enjoying rides, attractions, and stunning lake views. For lunch, stop by Gibsons Bar & Steakhouse for some classic American fare.
Evening
Conclude your day with a visit to the iconic sports venue, Wrigley Field. Enjoy dinner at Joe's Seafood, Prime Steak & Stone Crab.
Bedtime
Find amazing hotels in Chicago, Illinois.

Exploring Museums and Local Flavors

Morning
Start your day with a visit to the fascinating exhibits at the Museum of Science and Industry. Have breakfast at nearby café or coffee shop.
Afternoon
Head over to explore more art and culture at the historic site of 360 Chicago Observation Deck (Formerly John Hancock Observatory) 1208 . For lunch try out some local flavors from Smoque BBQ restaurant .
Evening
In evening , take leisurely walk through Lincoln Park Zoo 1211 followed by dining experience Quartino Ristorante & Wine Bar
Bedtime
Find amazing hotels in Chicago, Illinois.

Final Day of Chicago Delights

Morning
Begin your final day with a visit to Adler Planetarium, where you can explore the wonders of the universe. Enjoy breakfast at a nearby café or coffee shop.
Afternoon
Spend your afternoon at Shedd Aquarium, home to thousands of aquatic animals. For lunch, try Smoque BBQ, known for its delicious barbecue dishes.
Evening
End your trip with a visit to Second City for some world-class comedy. Have dinner at Quartino Ristorante & Wine Bar, offering Italian cuisine and an extensive wine list.
Bedtime
Find amazing hotels in Chicago, Illinois.
kayakFind the right stay during your trip.
Got a question about your trip?