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.

Kimpton Gray Hotel by IHG

Downtown Chicago

CA $1,501

per person

Aug 7 - Aug 11

found 2 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

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

Level Chicago Fulton Market

Downtown Chicago

CA $1,951

per person

Sep 12 - Sep 17

found 15 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Pendry Chicago

Downtown Chicago

CA $2,010

per person

Sep 6 - Sep 12

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) 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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $2,269

per person

Sep 1 - Sep 6

found 19 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $3,725

per person

Sep 12 - Sep 17

found 15 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

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

Thompson Chicago, by Hyatt

Downtown Chicago

CA $2,450

per person

Sep 12 - Sep 17

found 15 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, 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.

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 $1,501 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 $211

CA $251 total

Jul 1 - Jul 2

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 Grant Park and Millennium Park are located nearby.

Free WiFi

Restaurant

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $284

CA $380 total

Jul 6 - Jul 7

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

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $217

CA $305 total

Jul 5 - Jul 6

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

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