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.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $569

per person

Mar 17 - Mar 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

CA $1,837

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

Book a stay at this 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,019

per person

Mar 17 - Mar 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Book a stay at this 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.

The Peninsula Chicago

Downtown Chicago

CA $2,293

per person

Apr 1 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Downtown Chicago

CA $728

per person

Mar 17 - Mar 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Book a stay at this 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.

Pendry Chicago

Downtown Chicago

CA $700

per person

Mar 17 - Mar 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, 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.

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 $569 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 $135

CA $158 total

Jan 20 - Jan 21

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 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.

Free WiFi

Restaurant

Hilton Chicago

720 S Michigan Ave Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $181

CA $254 total

Feb 1 - Feb 2

includes taxes & fees

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 Millennium Park and Soldier Field are located nearby.

Pool

Hot tub

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $114

CA $133 total

Feb 1 - Feb 2

includes taxes & fees

Book a stay at this 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.

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