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.

Swissotel - Chicago

Downtown Chicago

CA $735

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Fairmont Chicago at Millennium Park

Downtown Chicago

CA $764

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

La Banque Hotel

CA $1,190

per person

Jun 11 - Jun 18

found 19 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.

The Royal Sonesta Chicago River North

Downtown Chicago

CA $806

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pendry Chicago

Downtown Chicago

CA $1,023

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,018

per person

Jul 1 - Jul 4

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue 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 $735 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 $135

CA $160 total

May 25 - May 26

includes taxes & fees

Book a stay at this 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

River Hotel

75 East Wacker Drive Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $143

CA $170 total

May 25 - May 26

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

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $119

CA $181 total

Apr 27 - Apr 28

includes taxes & fees

Book a stay at this 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.

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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