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 Chicago/Magnificent Mile Suites

Downtown Chicago

per person

Jul. 9 - Jul. 13

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul. 9 - Jul. 13

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Chicago (ORD)

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

Dorothy's

Lakeview

Save 100% on your flight

per person

Jun. 22 - Jun. 28

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.

Level Chicago – Old Town

Downtown Chicago

per person

Jun. 26 - Jul. 2

found 1 day ago

Roundtrip flight included

Vancouver (YVR) 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.

Arlo Chicago

Downtown Chicago

per person

Jul. 9 - Jul. 13

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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 $766 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 $175

CA $206 total

includes taxes & fees

May 12 - May 13

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

Holiday Inn Chicago Dwtn - The Mart by IHG

350 West Wolf Point Plaza, Building 2, Chicago, IL

Free cancellation

CA $247

CA $290 total

includes taxes & fees

May 26 - May 27

Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, 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.

Pool

Free WiFi

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St, Chicago, IL

CA $210

CA $291 total

includes taxes & fees

May 11 - May 12

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.