layla-imagelayla-logo
layla-logo

New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate 5-Day Chicago Exploration Itinerary

Ultimate 5-Day Chicago Exploration Itinerary Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and River Cruises

Morning
Begin your Chicago adventure with a hearty breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll to the historic Wrigley Building and the vibrant Michigan Avenue Bridge. Capture the morning light at the Chicago River as you prepare for an architectural journey.
Afternoon
Savor a delightful lunch at The Purple Pig, offering a menu of Mediterranean flavors. Following this, enjoy a family-friendly architectural cruise on the Chicago 45-Minute Family-Friendly Architecture River Cruise. Later, visit the iconic John Hancock Center and its 360 Chicago Observation Deck with a skip-the-line ticket.
Evening
Dine with a view at The Signature Room at the 95th, and then take an evening stroll at the lively Navy Pier. Conclude your day with the dazzling lights and sounds of the Centennial Wheel.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Wrigley Building

star4.39

click to access prices

Popular
activity-image

Chicago Riverwalk

star4.72

click to access prices

Popular
activity-image

Chicago River

star4.61

click to access prices

Popular
activity-image

Chicago 45-Minute Family-Friendly Architecture River Cruise

star4.68

click to access prices

Popular
activity-image

360 Chicago Observation Deck (Formerly John Hancock Observatory)

star4.17

click to access prices

Popular
activity-image

Navy Pier

star4.48

click to access prices

Museum Marvels and Scenic Walks

Morning
Enjoy a morning coffee and pastry at Lula Cafe before immersing yourself in the world of art at the renowned Art Institute of Chicago with a fast-pass ticket. Explore the nearby Millennium Park and its famous "Bean," the Cloud Gate.
Afternoon
For lunch, head to Eataly Chicago to experience a variety of Italian cuisines. Afterward, take a leisurely stroll along the Chicago Riverwalk and explore the hidden gems of the city on the Chicago Underground Pedway & Downtown Secrets Walking Tour.
Evening
Dine at the trendy Big Star for some of the best tacos in town. Cap off the night with a visit to the historic Wrigley Field, home of the Chicago Cubs, or enjoy live music at a local venue.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Art Institute of Chicago

star4.61

click to access prices

Popular
activity-image

Millennium Park

star4.69

click to access prices

Popular
activity-image

Chicago Riverwalk

star4.72

click to access prices

Popular
activity-image

Chicago Underground Pedway & Downtown Secrets Walking Tour

star4.73

click to access prices

Popular
activity-image

Wrigley Field

star4.86

click to access prices

Cultural Delights and Scenic Views

Morning
Start your day with a delicious breakfast at Little Goat Diner, known for its creative menu. Afterward, visit the serene Lincoln Park and the nearby Lincoln Park Zoo for a morning of leisurely exploration.
Afternoon
Have lunch at Girl & the Goat, an award-winning restaurant serving bold flavors. Then, enjoy the panoramic views of the city from the 360 Chicago Observation Deck with a sip and view ticket. Later, take a guided tour of the city's gangster and ghost history.
Evening
Dine at RPM Italian, known for its sleek ambiance and modern Italian dishes. Afterward, take a relaxing evening cruise on Lake Michigan with a buffet brunch, lunch, or dinner on the Odyssey Lake Michigan.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Lincoln Park & Zoo

star4.29

click to access prices

Popular
activity-image

360 Chicago Observation Deck (Formerly John Hancock Observatory)

star4.17

click to access prices

Popular
activity-image

Chicago Lake Michigan Buffet Brunch, Lunch or Dinner Cruise

star4.01

click to access prices

Culinary Exploration and Historic Tours

Morning
Enjoy a delightful breakfast at Cafe Ba-Ba-Reeba!, offering a taste of Spain in the heart of Chicago. Then, embark on a Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus to get an overview of the city's top attractions.
Afternoon
For lunch, indulge in the savory flavors of barbecue at Smoque BBQ. Then, satisfy your sweet tooth with a visit to the Museum of Ice Cream with a timed entrance ticket. Continue your culinary journey on the Chicago Favorite Foods Guided Walking Tour.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse known for its prime cuts. Conclude your day with a visit to the historic Chicago Theatre for a memorable performance.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

star4.28

click to access prices

Popular
activity-image

Chicago Museum of Ice Cream Entry Ticket

star4.09

click to access prices

Popular
activity-image

Chicago Classic Food Walking Tour with Bike or Kayak Rental

star4.82

click to access prices

Popular
activity-image

Chicago Theatre

star4.71

click to access prices

Final Day of Sights and Bites

Morning
Start your day with breakfast at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches. Then, take a morning walk along the Magnificent Mile and explore the upscale shops and boutiques.
Afternoon
For lunch, head to Pequod's Pizza to enjoy their famous caramelized crust pizza. Afterward, visit the Tribune Tower and the nearby Field Museum for an afternoon of history and culture.
Evening
Dine at Kuma's Corner, a rock music-themed burger bar with a heavy-metal vibe. End your trip with a visit to the Adler Planetarium to explore the wonders of the universe and enjoy the beautiful Chicago skyline at night.
Bedtime
Find amazing hotels in Chicago.
Popular
activity-image

The Magnificent Mile

star4.65

click to access prices

Popular
activity-image

Tribune Tower

star4.61

click to access prices

Popular
activity-image

Field Museum

star4.56

click to access prices

Popular
activity-image

Adler Planetarium

star4.61

click to access prices

Top Chicago Travel Videos

Adjacent Cities

IndianapolisLouisvilleNashvilleMemphisDallasAustinHouston

What others have been looking for

7 Days Exploring Historical Sites, Beaches, and Local Cuisine in Rhodos
Family Fun in Prague: 5-Day Itinerary for Teens
Culinary Delights of Veerayapalem in 5 Days
Scenic Delights in Muskegon and Grand Haven
5 Days in Nice and the Cote d’Azur
Cultural and Culinary Delights of Kochi, Munnar, and Alleppey in 4 Days
5 Days Exploring Sakleshpur's Natural Beauty
Philippines Adventure - 5 Days
3-Day Alaskan Adventure
3 Days of Walking and Good Food in NYC
5 Days of Adventure and Relaxation in Phuket
Lake Maggiore and Borromean Islands Delights
Ultimate 21-Day Cultural and Adventure Journey in Clark and Siargao
kayakFind the right stay during your trip.
Got a question about your trip?