Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Chicago Concert Getaway: Experience Justin Timberlake Live

Viewed by 104 travelers

Day 1: Arrival & City Exploration

Chicago, IL

10:00AM

Check into Hotel

Arrive in Chicago and check into your hotel, setting the stage for your city adventure and concert excitement.
Choose a centrally located hotel like the Hyatt Regency for convenience - approximately USD150 per night.
USD150, 30 minutes

11:00AM

Brunch at The Bongo Room

Kick off your trip with a delightful brunch at The Bongo Room, famous for its creative pancakes and luscious brunch options.
A quick 15-minute walk from your hotel.
USD20, 1 hour

12:30PM

Visit Art Institute of Chicago

Explore one of the oldest and largest art museums in the United States, filled with exquisite collections and famous artworks.
A taxi ride to the Art Institute takes about 10 minutes from brunch.
USD25, 2 hours

2:30PM

Stroll through Millennium Park

Take a leisurely walk through Millennium Park to admire the stunning architecture and the iconic Cloud Gate sculpture.
A 10-minute walk from the Art Institute.
Free, 1 hour

3:30PM

Coffee at Intelligentsia

Recharge with a refreshing cup of coffee from Intelligentsia, a local favourite known for its artisanal brews.
Walk to the nearby café in about 5 minutes.
USD5, 30 minutes

4:00PM

Explore Navy Pier

Head to the vibrant Navy Pier to explore shops, enjoy the view, and even consider a ride on the Ferris wheel for a bit of fun.
A taxi will get you there in about 10 minutes.
Free - USD15 for Ferris wheel, 2 hours

6:00PM

Dinner at Lou Malnati's

Savour Chicago's famous deep-dish pizza at Lou Malnati's for a classic dining experience before the concert.
A short taxi ride will take around 10 minutes.
USD30, 1 hour

7:00PM

Head to United Center

With dinner finished, make your way to the United Center to ensure you arrive in plenty of time for the concert.
Leave around 7 PM via taxi to arrive punctually.
USD15, 15 minutes

7:15PM

Arrive at United Center

Arrive early to find your seats and soak in the excitement before Justin Timberlake takes the stage.
You’re at the venue ahead of schedule.
Free, 30 minutes

7:45PM

Justin Timberlake Concert

Enjoy the electric atmosphere and the incredible performance by Justin Timberlake as he captivates the audience.
You're settled in and ready for a fantastic night ahead!
USD200, 2 hours 15 minutes

10:00PM

Return to Hotel

After the concert, make your way back to your hotel, buzzing from the exciting performance.
Catch a taxi to return, taking around 15 minutes.
USD15, 15 minutes
Find Hotels in Chicago

Day 2: Final Morning & Departure

Chicago, IL

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Fuel up with a hearty breakfast at Wildberry, famous for their pancakes and inventive breakfast dishes.
A 10-minute walk from your hotel.
USD20, 1 hour

9:30AM

Last-minute Shopping at Magnificent Mile

Enjoy some last-minute shopping along the Magnificent Mile, where you can find a mix of shops and boutiques.
A short taxi ride from breakfast will take you there in about 10 minutes.
Free (shopping as per preferences), 1 hour 30 minutes

11:00AM

Check-out and Head to Airport

Check out from your hotel and head to the airport to catch your flight home, filled with amazing memories.
Arrange a taxi from your hotel to O'Hare; the ride is approximately 30 minutes.
USD30, 30 minutes
Find Hotels in Chicago
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About Chicago, IL

Trip Packing List: Chicago (Late February 2026)
Packing List
Trip Packing List: Ahmedabad → Abu Dhabi → Chicago (4 Jun–11 Jul)
Packing List
Chicago Weather Guide: Mid-May Transitions & Lake Breezes
Weather Guide
Chicago Weather & Climate Guide: Seasons in the Windy City
Weather Guide
Full Guide to Michelin Star Cities: 2025 Updated List
Travel Expert
Global Michelin Cities & US Travel Tiers from New York
Travel Expert
Itinerary created by AI-assisted, human-reviewed

Plan Your Chicago, IL Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go