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.

Hampton Inn Chicago-Carol Stream

per person

Jul. 5 - Jul. 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this hotel in Carol Stream. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cosley Zoo and Dupage County Historical Museum are located nearby.

Arlo Chicago

Downtown Chicago

Save 100% on your flight

per person

May 23 - May 26

found 9 hours ago

Roundtrip flight included

Toronto (YTO) 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.

Dorothy's

Lakeview

Save 100% on your flight

per person

Jul. 5 - Jul. 8

found 19 hours ago

Roundtrip non-stop 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.

Hilton Garden Inn Hoffman Estates

per person

Jul. 5 - Jul. 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3-star hotel in Hoffman Estates. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Bridges of Poplar Creek Country Club are located nearby.

Hotel Indigo Chicago-Vernon Hills by IHG

per person

Jul. 5 - Jul. 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3.5-star boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Cuneo Mansion and Gardens and Conway Farms Golf Club 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 $771 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

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free cancellation

CA $172

CA $202 total

includes taxes & fees

Apr 20 - Apr 21

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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $207

CA $243 total

includes taxes & fees

Apr 21 - Apr 22

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

Swissotel - Chicago

323 E Wacker Dr, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $249

CA $333 total

includes taxes & fees

Apr 20 - Apr 21

Book a stay at this eco-certified 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.

Spa

Pet-friendly

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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.