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.

theWit Chicago, a Hilton Hotel

Downtown Chicago

per person

Jan. 30 - Feb. 4

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTZ) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jan. 30 - Feb. 4

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTZ) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Jan. 30 - Feb. 4

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTZ) 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.

Level Chicago – Old Town

Downtown Chicago

per person

Jan. 30 - Feb. 4

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTZ) to Chicago (ORD)

Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Palmer House a Hilton Hotel

Downtown Chicago

per person

Jan. 30 - Feb. 4

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTZ) to Chicago (ORD)

Book a stay at this spa 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.

Fairmont Chicago at Millennium Park

Downtown Chicago

per person

Jan. 30 - Feb. 4

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTZ) to Chicago (ORD)

Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 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.

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 $807 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

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $134

CA $157 total

includes taxes & fees

8 Dec - 9 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

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $189

CA $222 total

includes taxes & fees

10 Nov - 11 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.

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $135

CA $159 total

includes taxes & fees

9 Dec - 10 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

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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.