layla-imagelayla-logo
layla-logo

New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate Chicago Experience in 7 Days

Ultimate Chicago Experience in 7 Days Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks

Morning
Start your Chicago adventure with a delicious brunch at The Purple Pig, known for its Mediterranean flavors. Afterward, take a stroll to Millennium Park to see the famous Cloud Gate sculpture.
Afternoon
For lunch, enjoy a deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago to admire its world-class art collection.
Evening
In the evening, have a memorable dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a leisurely walk along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Millennium Park

star4.69

click to access prices

Popular
activity-image

Art Institute of Chicago

star4.61

click to access prices

Popular
activity-image

Chicago Riverwalk

star4.72

click to access prices

Architectural Marvels and Skyline Views

Morning
Enjoy a gourmet breakfast at Xoco, offering delicious Mexican cuisine. Then, embark on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's iconic architecture.
Afternoon
For lunch, savor the flavors of Italy at Eataly Chicago. Afterward, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Evening
Dine at The Signature Room at the 95th and enjoy a sophisticated meal with a view. End your day with a visit to the The Magnificent Mile for some evening shopping.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Chicago Architecture Center Cruise on Chicago's First Lady

star4.46

click to access prices

Popular
activity-image

360 Chicago Observation Deck (Formerly John Hancock Observatory)

star4.17

click to access prices

Popular
activity-image

The Magnificent Mile

star4.65

click to access prices

Cultural Immersion and Culinary Delights

Morning
Start your day with a delightful breakfast at Lula Cafe, a local favorite. Then, explore the Field Museum and delve into natural history and culture.
Afternoon
For lunch, experience the famous pastrami sandwich at Manny's Cafeteria & Delicatessen. Afterward, visit the Chicago Cultural Center and admire its stunning architecture.
Evening
Indulge in a dinner at Girl & the Goat, known for its creative dishes. Afterward, take a leisurely walk along the Chicago Riverwalk.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Field Museum

star4.56

click to access prices

Popular
activity-image

Chicago Cultural Center

star4.71

click to access prices

Popular
activity-image

Chicago Riverwalk

star4.72

click to access prices

Lakefront Serenity and Navy Pier Fun

Morning
Enjoy a peaceful breakfast at Lula Cafe before heading to Navy Pier for a morning of entertainment and the Chicago Children's Museum.
Afternoon
Have a delightful seafood lunch at Shaw's Crab House. Then, take a Chicago Architecture River Cruise to see the city's skyline from the water.
Evening
For dinner, savor the flavors of the sea at Joe's Seafood, Prime Steak & Stone Crab. Afterward, take a ride on the Centennial Wheel at Navy Pier for stunning views of the city.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Navy Pier

star4.48

click to access prices

Popular
activity-image

Chicago Architecture River Cruise Skip-the-Ticket Line

star4.83

click to access prices

Popular
activity-image

Chicago Navy Pier Centennial Wheel Regular & Express Ticket

star4.43

click to access prices

Gangsters, Ghosts, and Gourmet Dining

Morning
Start your day with a hearty breakfast at Wildberry Pancakes and Cafe. Then, embark on the Chicago Crime and Mob Tour to explore the city's notorious past.
Afternoon
Enjoy a unique food experience with the Chicago Gangsters and Food Tasting Walking Tour. Sample a variety of local dishes with a historical twist.
Evening
For dinner, dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, take a Chicago Hauntings Ghost Tour for a spine-chilling evening.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Fuji Safari Park

star0.00

click to access prices

Popular
activity-image

Chicago Gangsters and Food Tasting Walking Tour

star4.67

click to access prices

Popular
activity-image

Observation Deck at 300

star3.00

click to access prices

Museum Day and Culinary Delights

Morning
Have a leisurely breakfast at Yolk - South Loop before visiting the Museum of Science and Industry. Spend the morning exploring its fascinating exhibits.
Afternoon
For lunch, enjoy a farm-to-table experience at Eden. Afterward, visit the Adler Planetarium and enjoy the stunning views of the city skyline.
Evening
Dine at The Publican, a renowned restaurant known for its beer selection and pork dishes. After dinner, take a walk around the Lincoln Park Zoo.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Museum of Science and Industry

star4.31

click to access prices

Popular
activity-image

Adler Planetarium

star4.61

click to access prices

Popular
activity-image

Lincoln Park & Zoo

star4.29

click to access prices

Farewell to Chicago with a Culinary Journey

Morning
Enjoy a final breakfast at Au Cheval, famous for its decadent burgers. Then, take a relaxing walk in Grant Park before your departure.
Afternoon
For a memorable last meal in Chicago, have lunch at Girl & the Goat, known for its bold flavors and innovative dishes. Afterward, visit the Willis Tower Skydeck for one last look at the city from above.
Evening
Conclude your Chicago journey with a farewell dinner at Alinea, a three-Michelin-star restaurant known for its avant-garde cuisine. After dinner, take a stroll along the Chicago Riverwalk to savor the city's ambiance one last time.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Grant Park

star4.70

click to access prices

Popular
activity-image

Skydeck Chicago at Willis Tower (Sears Tower)

star4.27

click to access prices

Popular
activity-image

Chicago Riverwalk

star4.72

click to access prices

Top Chicago Travel Videos

Adjacent Cities

IndianapolisLouisvilleNashvilleMemphisDallasAustinHouston

What others have been looking for

7 Days in Jaipur Rajasthan
Ultimate 5-Day Malta Island Adventure
Osaka, Kyoto, Nara Adventure - 7 Days
New Year's Celebration in London
Ultimate 10-Day Miami and Orlando Adventure
Sanur Serenity and Adventure: A 6-Day Bali Escape
5-Day Amritsar and Delhi Adventure
Historic Treasure Hunts and Culinary Delights in Loughborough
5 Days Exploring Dubai
Discovering the Charms of Prague in Three Weeks
Jerusalem Adventure - 5 Days
Spiritual Journey in the Himalayas
Boston Adventure 4 Days
4-Day Boston Adventure
kayakFind the right stay during your trip.
Got a question about your trip?