NOW Arena Vacation Deals: NOW Arena, Chicago Holidays

NOW Arena vacation package deals

Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $687

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $707

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.

The Peninsula Chicago

Downtown Chicago

CA $1,902

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop 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 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,543

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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.

Level Chicago – Old Town

Downtown Chicago

CA $841

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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 $808

per person

Jan 31 - Feb 6

found 1 day ago

Roundtrip non-stop 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.

Frequently asked questions

How much are vacation packages to Sears Center?

If you'd like to enjoy hassle-free planning and huge savings, our CA $687 Sears Center vacation package will be perfect for you. With your hotel and flights sorted, organizing your getaway around this fabulous attraction is easier than ever.

Where can I get the best vacation package deals for Sears Center?

No matter how you travel, Travelocity can help you lock in a great Sears Center package deal. All you have to do is pick and choose between our 400 air carriers and 665,000 properties across the globe.

Why should I purchase my Sears Center vacation bundle via Travelocity?

Because we believe in creating unforgettable vacation experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our customer care is available 24/7 to ensure you're being well taken care of. We also have an amazing Price Match Guarantee, so you can book your vacation knowing you've scored the best deal around. How? If you find a lower price, we'll match it!

Can I go on vacation to Sears Center at this time?

Our team has all the local knowledge to help make your travel dreams come true, so before arranging a ticket to Sears Center, look over our Covid-19 Travel Advisor. This is where you can get up-to-date info on travel restrictions, quarantine policies and other useful advice.

Top NOW Arena hotel deals

Hampton Inn & Suites Chicago/Hoffman Estates

2825 Greenspoint Pkwy Hoffman Estates IL

Free cancellation

Reserve now, pay when you stay

CA $113

CA $127 total

Dec 25 - Dec 26

includes taxes & fees

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

Pool

Breakfast included

Embassy Suites by Hilton Chicago Schaumburg Woodfield

1939 N Meacham Rd Schaumburg IL

Free cancellation

Reserve now, pay when you stay

CA $157

CA $180 total

Dec 26 - Dec 27

includes taxes & fees

Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Woodfield Mall and Jump Zone are located nearby.

Pool

Breakfast included

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

Free cancellation

Reserve now, pay when you stay

CA $102

CA $118 total

Jan 2 - Jan 3, 2026

includes taxes & fees

Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Woodfield Mall and AMC Streets Of Woodfield 20 are located nearby.

Pool

Breakfast included

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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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