New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

4-Day Chicago Adventure with Best Friends

4-Day Chicago Adventure with Best Friends Itinerary

Published: 2024 Feb 29

City Icons and Sky-High Views

Morning
Start your day with a delightful brunch at Lula Cafe, known for its farm-to-table dishes and cozy atmosphere. Afterward, head to the iconic Wrigley Building and take a stroll along the Chicago Riverwalk, enjoying the views of the city's impressive architecture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago, home to an extensive collection of art, including the renowned "American Gothic" painting.
Evening
In the evening, enjoy a gourmet dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, experience the city's nightlife at the lively The Magnificent Mile, known for its upscale shops and vibrant atmosphere.
Bedtime
Find amazing hotels in Chicago.

Cultural Exploration and River Cruise

Morning
Start your day with a visit to the Museum of Science and Industry, where you can explore interactive exhibits and learn about scientific innovations. For a quick bite, grab lunch at Pequod's Pizza, famous for its caramelized crust.
Afternoon
Embark on a Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's skyline from a unique perspective. After the cruise, take a leisurely walk in Millennium Park and take a selfie at the iconic "Bean" sculpture.
Evening
For dinner, indulge in Mediterranean cuisine at The Purple Pig, known for its inventive small plates. Afterward, enjoy a nightcap at The Signature Room at the 95th, offering breathtaking views of the city from the 95th floor of the John Hancock Center.
Bedtime
Find amazing hotels in Chicago.

Museum Marvels and Haunted History

Morning
Start your day with a hearty breakfast at Little Goat Diner, a contemporary diner with a creative menu. Then, visit the Field Museum, where you can explore exhibits on natural history and cultural artifacts.
Afternoon
Enjoy a guided Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's darker history and mysterious stories. For lunch, head to Big Star for delicious tacos and a laid-back atmosphere.
Evening
For a unique dining experience, make a reservation at Girl & the Goat, known for its bold flavors and innovative dishes. Afterward, take a stroll along the Chicago River and enjoy the city lights reflecting on the water.
Bedtime
Find amazing hotels in Chicago.

Lakefront Beauty and Culinary Delights

Morning
Start your day with a visit to the Shedd Aquarium, where you can marvel at a diverse range of aquatic species. For a quick snack, grab a pastry at Xoco, known for its Mexican-inspired cuisine.
Afternoon
Explore the Navy Pier, where you can ride the Chicago Navy Pier Centennial Wheel Regular & Express Ticket for panoramic views of the city. For lunch, enjoy tapas at Cafe Ba-Ba-Reeba!, a lively Spanish restaurant.
Evening
End your trip with a memorable dinner at Au Cheval, famous for its mouthwatering burgers and upscale diner ambiance. Afterward, take a walk along the Chicago River and enjoy the city's skyline at night.
Bedtime
Find amazing hotels in Chicago.

Adjacent Cities

kayakFind the right stay during your trip.
Got a question about your trip?