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.

Hilton Garden Inn Chicago North Shore/Evanston

per person

Jan. 1 - Jan. 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Aragon Ballroom and Riviera Theatre are located nearby.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Jan. 15 - Jan. 20

found 20 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Hilton Orrington / Evanston

Save 100% on your flight

per person

Jan. 1 - Jan. 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clark Street Beach and Halim Time & Glass Museum are located nearby.

Hilton Chicago

Downtown Chicago

per person

Jan. 15 - Jan. 20

found 20 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

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 Grant Park and Art Institute of Chicago are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Feb. 3 - Feb. 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

21c Museum Hotel Chicago

Downtown Chicago

per person

Jan. 15 - Jan. 20

found 20 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. 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 $726 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 $180

CA $211 total

includes taxes & fees

25 Nov - 26 Nov

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.

Free WiFi

Restaurant

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $134

CA $158 total

includes taxes & fees

24 Dec - 25 Dec

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $135

CA $159 total

includes taxes & fees

25 Dec - 26 Dec

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue 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.