New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate 4-Day Chicago Adventure

Ultimate 4-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and Riverfront Delights

Morning
Begin your Chicago journey with breathtaking views from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Afterward, enjoy a delightful breakfast at Cindy's Rooftop, where you can savor delicious food with a stunning view of the city.
Afternoon
Immerse yourself in the city's history and architecture with a visit to the Wrigley Building and a stroll along the Chicago Riverwalk. For lunch, head to City Social for a sophisticated dining experience with panoramic city views.
Evening
Spend a magical evening at the Chicago Theatre for a show. Beforehand, indulge in a pre-theater dinner at Lockwood Restaurant & Bar, known for its elegant ambiance and contemporary American cuisine.
Bedtime
Find amazing hotels in Chicago.

Art, Parks, and Cultural Gems

Morning
Start your day with a visit to the world-renowned Art Institute of Chicago, where you can admire masterpieces. Enjoy a hearty breakfast at Doc B's Restaurant (River North) to fuel up for the day.
Afternoon
After the museum, take a leisurely walk to Millennium Park to see the iconic Cloud Gate sculpture. For lunch, head to The Gage, located just steps away, offering a menu of classic American dishes.
Evening
Explore the beautiful greenery of Grant Park and then enjoy an evening at the Adler Planetarium for a celestial experience. Conclude the day with dinner at FireLake Grill House and Cocktail Bar, known for its Midwestern-inspired cuisine.
Bedtime
Find amazing hotels in Chicago.

Lakefront Serenity and Museum Marvels

Morning
Take a morning walk at the serene Lincoln Park & Zoo, followed by a delightful breakfast at Plymouth Restaurant & Rooftop Bar, offering a cozy atmosphere and a rooftop view.
Afternoon
Visit the Field Museum to immerse yourself in natural history. For lunch, head to South Branch Tavern & Grille (The Loop - Chicago) for a relaxed riverside dining experience.
Evening
Enjoy the marine wonders at the Shedd Aquarium. Cap off the day with a dinner cruise on the Chicago River, where you can enjoy the city's skyline while dining on a luxurious boat.
Bedtime
Find amazing hotels in Chicago.

Parks, Sports, and Culinary Delights

Morning
Start with a morning jog or walk at Grant Park, then have a hearty breakfast at Sweetwater Tavern & Grille (Michigan Plaza - Chicago).
Afternoon
Experience the lively atmosphere of Navy Pier and have lunch at Billy Goat Tavern (Millennium Park), a Chicago classic known for its "Cheezborger." Afterward, enjoy the attractions and the stunning views of Lake Michigan.
Evening
Conclude your trip with a visit to the historic Wrigley Field for a baseball game (if in season). For dinner, savor the flavors of Chicago at Burger Bar Chicago, offering a variety of gourmet burgers and a relaxed ambiance.
Bedtime
Find amazing hotels in Chicago.

Top Chicago Travel Videos

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