New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Exploring Chicago's Landmarks and Cuisine

Exploring Chicago's Landmarks and Cuisine Itinerary

Last updated: 2024 Jun 14

Iconic Skyline and River Views

Morning
Begin your Chicago adventure with a hearty breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take in the breathtaking city views from the 360 Chicago Observation Deck (Formerly John Hancock Observatory), where you'll enjoy a skip-the-line experience.
Afternoon
For lunch, savor the flavors of Italy at Eataly Chicago, an expansive marketplace with a variety of dining options. Spend your afternoon on the water with the Chicago River 1.5-Hour Guided Architecture Cruise, learning about the city's renowned architecture.
Evening
As the sun sets, dine at The Signature Room at the 95th, offering exquisite cuisine and stunning panoramic views. End your night with a leisurely stroll along the Chicago Riverwalk, taking in the vibrant atmosphere.
Bedtime
Find amazing hotels in Chicago.
Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago
star4.17

360 Chicago Observation Deck (Formerly John Hancock Observatory)

Book Now
Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago
star4.77

Chicago River 1.5-Hour Guided Architecture Cruise

Book Now
next arrow

Museums and Cultural Highlights

Morning
Start with a delicious breakfast at The Purple Pig, known for its Mediterranean-inspired dishes. Then, immerse yourself in art at the world-renowned Art Institute of Chicago with a fast-pass ticket.
Afternoon
Enjoy a lunchtime cruise with the Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise, taking in the city's skyline from the water. Afterward, visit the aquatic wonders at the Shedd Aquarium.
Evening
Dine at Girl & the Goat, an award-winning restaurant serving innovative cuisine. Cap off the night with a visit to the historic The Chicago Theatre, known for its stunning architecture and performances.
Bedtime
Find amazing hotels in Chicago.
Visit Art Institute of Chicago in Chicago
star4.61

Art Institute of Chicago

Book Now
Visit Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise in Chicago
star4.01

Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise

Book Now
next arrow

Historic Landmarks and Evening Entertainment

Morning
Enjoy a classic Chicago breakfast at Portillo's Hot Dogs, famous for its hot dogs and Italian beef sandwiches. Then, take a guided tour of the iconic Chicago Theatre for a behind-the-scenes look.
Afternoon
Have lunch at Giordano's, a Chicago institution known for its mouthwatering stuffed deep-dish pizza. Spend your afternoon exploring the history and exhibits at the Field Museum or the nearby Adler Planetarium.
Evening
For dinner, head to RPM Italian to indulge in modern Italian cuisine. Later, experience Chicago's vibrant nightlife with live music at Buddy Guy's Legends, an iconic blues club.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Theatre in Chicago
star4.71

Chicago Theatre

Book Now
Visit Field Museum in Chicago
star4.56

Field Museum

Book Now
next arrow

Culinary Delights and Scenic Views

Morning
Start your day with a visit to Millennium Park, where you can enjoy the famous "Bean" sculpture and the serene Lurie Garden. Grab breakfast at Lula Cafe, a neighborhood spot known for its creative dishes and laid-back atmosphere.
Afternoon
Explore the vibrant neighborhood of Wicker Park and enjoy lunch at Big Star, a popular spot for gourmet tacos and craft cocktails. Then, take in the city from a different angle at the Chicago 360 Chicago Observation Deck, also known as the John Hancock Center.
Evening
Dine at Longman & Eagle, a Michelin-starred gastropub known for its farm-to-table menu. Afterward, take a leisurely walk through the historic Wrigleyville area, home to the famous Wrigley Field.
Bedtime
Find amazing hotels in Chicago.
Visit Millennium Park in Chicago
star4.69

Millennium Park

Book Now
Visit Chicago 360 Chicago Observation Deck General Admission in Chicago
star4.37

Chicago 360 Chicago Observation Deck

Book Now
next arrow

Neighborhood Exploration and Local Flavors

Morning
Start your final day with breakfast at Kuma's Corner, a rock 'n' roll burger bar known for its unique, heavy metal-inspired menu. Then, take a stroll through the charming Lincoln Park and visit the animals at the Lincoln Park Zoo, one of the oldest zoos in the country.
Afternoon
For lunch, head to Smoque BBQ and indulge in some of the best slow-smoked meats in the city. Afterward, explore the boutiques and cafés of the upscale Magnificent Mile shopping district.
Evening
Dine at Little Goat Diner, a casual spot with a menu full of inventive, fun dishes. End your trip with a relaxing evening cruise on the Chicago River, taking in the city's stunning architecture and lights.
Bedtime
Find amazing hotels in Chicago.
Visit Lincoln Park & Zoo in Chicago
star4.29

Lincoln Park Zoo

Book Now
Visit The Magnificent Mile in Chicago
star4.65

Magnificent Mile

Book Now
next arrow

Day Trip to Evanston's Cultural Gems

Morning
Begin your day with a delightful breakfast at Bangers & Lace, known for its craft beer and artisanal sausages. Then, take a morning stroll through the beautiful Chicago Botanic Garden, enjoying the serene landscapes and diverse flora.
Afternoon
For lunch, visit Taco Diablo and savor their creative, gourmet tacos in a vibrant setting. Spend your afternoon exploring the fascinating exhibits at the Mitchell Museum of the American Indian, learning about the rich cultural heritage of indigenous peoples.
Evening
Dine at Templestowe Pub, a cozy gastropub offering a menu of elevated comfort food. Wrap up your day with a performance at the renowned Paramount Theatre, enjoying a show in this historic and elegant venue.
Bedtime
Find amazing hotels in Evanston, Illinois.
Visit South Beach in Evanston, Illinois
star4.61

Paramount Theatre

Book Now
next arrow

Discovering the Architectural Wonders of Oak Park

Morning
Start your morning with a delicious breakfast at Hemmingway's Bistro, where you can enjoy classic French dishes in a charming setting. Then, embark on a guided tour of the Frank Lloyd Wright Home and Studio, exploring the birthplace of American architecture.
Afternoon
For lunch, visit Cooper's Hawk Winery & Restaurant and indulge in a menu of contemporary American cuisine paired with their own handcrafted wines. Afterward, take a leisurely walk through the picturesque Lake Street and Downtown Oak Park, exploring the boutiques and galleries.
Evening
Dine at Pastoral Artisan Cheese, Bread & Wine, a unique restaurant offering a menu of gourmet cheeses, charcuterie, and sandwiches. End your day with a performance at the Oak Park Conservatory, enjoying the serene atmosphere and beautiful floral displays.
Bedtime
Find amazing hotels in Oak Park, Illinois.
Visit Palma Private Guided Walking Tour in Oak Park, Illinois
star4.85

Frank Lloyd Wright Home and Studio

Book Now
Visit Chicago Riverwalk in Oak Park, Illinois
star4.72

Lake Street

Book Now
next arrow

Top Chicago Travel Videos

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