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.

Pendry Chicago

Downtown Chicago

CA $497

per person

Jan 16 - Jan 18

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,415

per person

Dec 18 - Dec 22

found 24 hours 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Park Hyatt Chicago

Downtown Chicago

CA $1,391

per person

Dec 18 - Dec 22

found 24 hours 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.

Viceroy Chicago

Downtown Chicago

CA $1,051

per person

Dec 23 - Dec 28

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $617

per person

Dec 23 - Dec 28

found 22 hours 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.

Level Chicago – Old Town

Downtown Chicago

CA $905

per person

Dec 19 - Dec 23

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.

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 $497 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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $166

CA $194 total

Nov 23 - Nov 24

includes taxes & fees

Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pool

Breakfast included

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $226

CA $265 total

Nov 2 - Nov 3

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 Millennium Park are located nearby.

Free WiFi

Restaurant

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $139

CA $208 total

Nov 25 - Nov 26

includes taxes & fees

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

Pet-friendly

Air conditioning

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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.

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