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 Orrington / Evanston

Downtown Evanston

CA $523

per person

Feb 28 - Mar 4

found 12 hours ago

Roundtrip flight included

Seattle (SEA) to Chicago (ORD)

Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clark Street Beach and Halim Time & Glass Museum are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,399

per person

Feb 27 - Mar 4

found 7 hours ago

Roundtrip flight included

Seattle (SEA) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $620

per person

Feb 28 - Mar 4

found 12 hours ago

Roundtrip flight included

Seattle (SEA) 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.

The Peninsula Chicago

Downtown Chicago

CA $1,838

per person

Feb 27 - Mar 4

found 11 hours ago

Roundtrip flight included

Seattle (SEA) 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.

The Langham, Chicago

Downtown Chicago

CA $1,401

per person

Feb 27 - Mar 4

found 7 hours ago

Roundtrip flight included

Seattle (SEA) 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.

Waldorf Astoria Chicago

Downtown Chicago

CA $1,542

per person

Feb 27 - Mar 4

found 12 hours ago

Roundtrip flight included

Seattle (SEA) 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.

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 $523 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 $186

CA $218 total

Feb 14 - Feb 15

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 $180

CA $251 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

The Royal Sonesta Chicago Downtown

71 E Wacker Dr Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $184

CA $259 total

Feb 7 - Feb 8

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff 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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