New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Ultimate Chicago Experience with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Chicago's Architectural Marvels and Skyline Views
Morning
Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a Chicago Architecture River Cruise Skip-the-Ticket Line to admire the city's iconic architecture from the water.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the Art Institute of Chicago to explore its world-class art collection.
Evening
Enjoy a gourmet dinner at Alinea, a three-Michelin-starred restaurant offering a unique dining experience. End your day with a bird's eye view of the city from the 360 Chicago Observation Deck (Formerly John Hancock Observatory).
Bedtime
Find amazing hotels in Chicago.
Popular
Chicago Architecture River Cruise Skip-the-Ticket Line
click to access prices
Popular
Art Institute of Chicago
click to access prices
Popular
360 Chicago Observation Deck (Formerly John Hancock Observatory)
click to access prices
Cultural Immersion in the Windy City
Morning
Start your day with a delicious breakfast at Lula Cafe, a popular spot for farm-to-table cuisine. Then, take a leisurely walk through Millennium Park and visit the famous The Bean.
Afternoon
For lunch, enjoy a variety of options at Eataly Chicago, a vibrant Italian marketplace. Spend the afternoon exploring the Field Museum and the Shedd Aquarium.
Evening
Dine at The Publican, known for its eclectic menu and extensive beer selection. Afterward, take a stroll down the Chicago Riverwalk and enjoy the city lights.
Bedtime
Find amazing hotels in Chicago.
Popular
Millennium Park
click to access prices
Popular
Field Museum
click to access prices
Popular
Shedd Aquarium
click to access prices
Popular
Chicago Riverwalk
click to access prices
Iconic Landmarks and Culinary Delights
Morning
Indulge in a classic Chicago breakfast at Au Cheval, famous for its decadent dishes. Then, visit the Willis Tower Skydeck and The Ledge for panoramic views of the city.
Afternoon
For lunch, try the award-winning burgers at Kuma's Corner. Afterward, explore the historic Wrigley Field on a guided tour.
Evening
Enjoy a pre-theater dinner at Girl & The Goat before attending a show at the iconic Chicago Theatre.
Bedtime
Find amazing hotels in Chicago.
Popular
Chicago Willis Tower Skydeck and The Ledge Ticket
click to access prices
Popular
Wrigley Field
click to access prices
Popular
Chicago Theatre
click to access prices
Culinary Delights and Neighborhood Exploration
Morning
Start your day with a leisurely brunch at Little Goat Diner, a favorite for its creative comfort food. Then, take a guided walking tour of the Chicago Loop and the Chicago Cultural Center.
Afternoon
For a late lunch, head to Giordano's for their famous stuffed deep-dish pizza. Spend the afternoon exploring the vibrant neighborhoods of Wicker Park and Bucktown.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, experience the city's nightlife in the trendy River North district.
Bedtime
Find amazing hotels in Chicago.
Popular
Chicago Loop
click to access prices
Popular
Chicago Cultural Center
click to access prices
A Day of Adventure and Thrills
Morning
Enjoy a hearty breakfast at Big Star, known for its tacos and whiskey selection. Then, spend the day at Six Flags Great America, experiencing the thrilling rides and attractions.
Afternoon
Have a fun and casual lunch at the park. Afterward, continue to enjoy the various rides and shows.
Evening
For dinner, try the barbecue at Smoque BBQ, a local favorite. Afterward, relax at your hotel and reminisce about the day's adventures.
Bedtime
Find amazing hotels in Chicago.
Relaxation and Culinary Exploration
Morning
Start your day with a leisurely breakfast at Longman & Eagle, known for its farm-to-table fare. Then, take a stroll through the serene Lincoln Park and visit the Lincoln Park Zoo.
Afternoon
Enjoy a picnic lunch in the park. Afterward, explore the charming Old Town neighborhood and its boutiques and cafes.
Evening
Dine at The Signature Room at the 95th, where you can enjoy stunning views of the city. After dinner, take a romantic Lake Michigan Skyline Cruise.
Bedtime
Find amazing hotels in Chicago.
Popular
Lincoln Park & Zoo
click to access prices
Popular
Lincoln Park & Zoo
click to access prices
Popular
Second City
click to access prices
Popular
Chicago Lake Michigan Skyline Cruise
click to access prices
Culinary Delights and Cultural Experiences
Morning
Start your day with a delicious brunch at Cafe Ba-Ba-Reeba!, known for its Spanish tapas. Then, visit the Chicago History Museum to learn about the city's rich past.
Afternoon
For lunch, enjoy the vibrant atmosphere at Xoco, a popular spot for Mexican street food. Spend the afternoon exploring the Chicago Riverwalk and taking in the views.
Evening
Dine at Frontera Grill, a renowned Mexican restaurant. Afterward, take a Chicago River Guided Sunset Cocktail & Architecture Tour for a unique perspective of the city.
Bedtime
Find amazing hotels in Chicago.
Popular
Chicago Riverwalk
click to access prices
Popular
Chicago River Guided Sunset Cocktail & Architecture Tour
click to access prices
A Day of Art and Culinary Exploration
Morning
Begin your day with a visit to the Museum of Contemporary Art and enjoy the cutting-edge exhibitions. For brunch, head to Lula Cafe for their creative and seasonal dishes.
Afternoon
Explore the River North art galleries and boutiques. For a late lunch, try the Italian cuisine at RPM Italian.
Evening
Dine at Girl & The Goat, a top-rated restaurant known for its bold flavors. After dinner, take a leisurely walk along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
Popular
Chicago Riverwalk
click to access prices
Farewell to Chicago with Culinary Delights
Morning
Enjoy a final breakfast at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs. Then, take a Chicago River 1.5-Hour Guided Architecture Cruise to say goodbye to the city's skyline.
Afternoon
For lunch, indulge in the famous pastrami sandwich at Manny's Cafeteria & Delicatessen. Spend the afternoon shopping along The Magnificent Mile and visiting the John Hancock Center.
Evening
End your Chicago adventure with a memorable dinner at Alinea, a three-Michelin-starred restaurant. Afterward, take a final stroll along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
Popular
Chicago River 1.5-Hour Guided Architecture Cruise
click to access prices
Popular
The Magnificent Mile
click to access prices
Popular
South Beach
click to access prices
Popular
Chicago Riverwalk
click to access prices
Departure Day with a Taste of Chicago
Morning
On your last day, enjoy a classic Chicago breakfast at Au Cheval, known for its indulgent dishes. Take a leisurely walk through Grant Park and visit the Buckingham Fountain.
Afternoon
For lunch, savor the flavors of the city at Giordano's with their famous stuffed deep-dish pizza. Spend your final afternoon exploring the Chicago Riverwalk and taking in the sights.
Evening
Conclude your trip with a farewell dinner at Gibsons Bar & Steakhouse, a Chicago institution. Reflect on your time in the city and savor the last moments of your Chicago experience.
Bedtime
Find amazing hotels in Chicago.
Popular
Grant Park
click to access prices
Popular
Palma Private Guided Walking Tour
click to access prices
Popular
Chicago Riverwalk
click to access prices
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.