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.

The Wade

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

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

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4-star boutique 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 Grant Park and Art Institute of Chicago are located nearby.

Park Hyatt Chicago

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). 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 $960 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 $243

CA $285 total

Aug 4 - Aug 5

includes taxes & fees

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

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

CA $206

CA $242 total

Aug 24 - Aug 25

includes taxes & fees

Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Pet-friendly

Free WiFi

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Free cancellation

CA $341

CA $444 total

Aug 10 - Aug 11

includes taxes & fees

Stay at this 4.5-star 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.

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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.