Willis Tower Vacation Deals: Willis Tower, Downtown Chicago Holidays

Willis Tower vacation package deals

Price found within the past 48 hours. Click for updated prices.

Sonder by Marriott Bonvoy The Burnham Apartments Loop

Downtown Chicago

CA $590

per person

Apr 16 - Apr 19

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this aparthotel in Chicago. Enjoy a fitness center, concierge services, and premium bedding. Our guests praise the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $778

per person

Apr 16 - Apr 19

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pendry Chicago

Downtown Chicago

CA $777

per person

Apr 16 - Apr 19

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

JW Marriott Chicago

Downtown Chicago

CA $860

per person

Apr 16 - Apr 19

found 1 hour ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

CA $1,113

per person

Apr 10 - Apr 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

CA $1,013

per person

Apr 10 - Apr 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Frequently asked questions

How much are vacation packages to Willis Tower?

Save on your visit to Willis Tower by combining your flights and hotel into a CA $590 package deal. With all that spare cash jangling around in your pocket, why not stay for a while longer and discover even more?

Where can I get the best vacation package deals for Willis Tower?

Picking up the best package deal to Willis Tower is easy with Travelocity. With access to 400 air carriers and 665,000 properties all over the world, you're flush with choice when selecting your flights and hotels.

Why should I book my Willis Tower vacation bundle with Travelocity?

From incredible destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 support will also ensure you're being taken care of before, during and after your vacation. And don't worry if you spot a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.

Can I go on vacation to Willis Tower at this time?

Discover all the info that's important relating to quarantine policies and travel restrictions ahead of your flight to Willis Tower. Our Covid-19 Travel Advisor is full of advice to help make your trip as hassle-free as possible.

Top Willis Tower hotel deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $190

CA $223 total

Feb 14 - Feb 15

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Free WiFi

Restaurant

Hilton Chicago

720 S Michigan Ave Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $189

CA $261 total

Feb 21 - Feb 22

includes taxes & fees

Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.

Pool

Hot tub

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $183

CA $249 total

Feb 21 - Feb 22

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Pool

Spa

Don't see what you're looking for?

See all available properties in Willis Tower

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do in Chicago