New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate 6-Day Chicago and Beyond Adventure

Ultimate 6-Day Chicago and Beyond Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and River Cruise

Morning
Begin your Chicago adventure with a breathtaking view from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Afterward, enjoy a hearty breakfast at Staytion Market & Bar in the Loop.
Afternoon
Immerse yourself in the city's architecture with a Chicago River 1.5-Hour Guided Architecture Cruise. Post-cruise, savor a classic Chicago-style lunch at Billy Goat Tavern (The Original).
Evening
Stroll along the Chicago Riverwalk and head to The Magnificent Mile for some upscale shopping. For dinner, indulge in the vibrant atmosphere and cuisine at Cindy's Rooftop.
Bedtime
Find amazing hotels in Chicago.

Cultural Delights and Lakefront Serenity

Morning
Explore the world-class exhibits at the Art Institute of Chicago and then take a leisurely walk in the serene Millennium Park. Enjoy a delightful breakfast at About Last Knife.
Afternoon
After the park, visit the historic Wrigley Building and then head to Navy Pier for a fun-filled afternoon. Have lunch with a view at Terrace 16.
Evening
Witness the grandeur of the city's theater scene with a show at the Chicago Theatre. For dinner, savor the flavors of Chicago at 312 Chicago.
Bedtime
Find amazing hotels in Chicago.

Wildlife, History, and Evening Jazz

Morning
Spend your morning at the Lincoln Park & Zoo, enjoying the company of diverse wildlife. For breakfast, visit Sweetwater Tavern & Grille (Michigan Plaza - Chicago) for a delightful start to your day.
Afternoon
Dive into history at the Field Museum and then have a relaxed lunch at Miller's Pub. Afterward, take a walk to the nearby Adler Planetarium for a celestial experience.
Evening
Conclude your day with a soulful jazz performance at The Green Mill, a historic jazz club. For dinner, head to 676 Restaurant & Bar for a sophisticated dining experience.
Bedtime
Find amazing hotels in Chicago.

Sports, Parks, and Evening Lights

Morning
Start with a visit to the legendary Wrigley Field for a guided tour. Then, enjoy a breakfast at FireLake Grill House and Cocktail Bar.
Afternoon
After the stadium, take a relaxing walk in Grant Park and visit the serene Buckingham Fountain. For lunch, head to State and Lake Chicago Tavern.
Evening
Experience the city's skyline from a different perspective at Skydeck Chicago at Willis Tower (Sears Tower). Later, enjoy a fine dining experience at Travelle at The Langham, Chicago.
Bedtime
Find amazing hotels in Chicago.

Day of Choice and Culinary Exploration

Morning
Today is your day of choice. You can opt for a morning helicopter tour of the Chicago skyline or enjoy a leisurely morning at your own pace. For breakfast, try the delightful offerings at Long Room Chicago.
Afternoon
Explore the city's culinary scene with a Chicago Favorite Foods Guided Walking Tour. Sample a variety of local dishes and gain insights into the city's food culture. For a more relaxed afternoon, you can also visit the Chicago Museum of Ice Cream.
Evening
Reflect on your trip over a sumptuous dinner at The Gage, known for its diverse menu and elegant ambiance.
Bedtime
Find amazing hotels in Chicago.

Chicago's Hidden Gems and Farewell Dinner

Morning
Discover the lesser-known side of Chicago with a visit to Marina City, the innovative urban complex. Enjoy a delightful breakfast at The Franklin Room.
Afternoon
Take a guided tour to explore the city's mob and crime history with the Chicago Mob and Crime Bus Tour. For lunch, indulge in the flavors of Elephant & Castle.
Evening
Conclude your Chicago journey with a memorable dinner at Lockwood Restaurant & Bar, where you can savor the culinary creations in a sophisticated setting.
Bedtime
Find amazing hotels in Chicago.

Top Chicago Travel Videos

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