Chicago Theatre Vacation Deals: Chicago Theatre, Downtown Chicago Holidays

Chicago Theatre vacation package deals

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

Hilton Chicago O'Hare Airport

O'Hare

per person

May 16 - May 19

found 6 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Hyatt Place Chicago-South/University Medical Center

Hyde Park

Save 100% on your flight

per person

May 15 - May 19

just found

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.

The Chicago Hotel Collection River North

Downtown Chicago

per person

May 15 - May 19

just found

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3-star hotel in Chicago. Enjoy free WiFi, a fitness center, and 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.

Sophy Hyde Park

Hyde Park

Save 100% on your flight

per person

May 15 - May 19

just found

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 4-star luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Soldier Field and Chicago Museum of Science and Industry are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Apr. 23 - Apr. 27

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 5-star 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

per person

Apr. 25 - Apr. 28

just found

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 5-star 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.

Frequently asked questions

How much are vacation packages to Chicago Theatre?

Score an express ticket to an impressive deal with Travelocity’s CA $863 Chicago Theatre vacation package. Not only will you save plenty on your return flights and hotel, you can also add on one or two interesting local activities or even a rental vehicle.

Where can I get the best vacation package deals for Chicago Theatre?

No matter what you enjoy doing, Travelocity can help you get the perfect Chicago Theatre package deal. All you need to do is pick and choose between our 400 air carriers and 665,000 properties worldwide.

Why should I book my Chicago Theatre vacation package with Travelocity?

Whether you’re on the hunt for the ultimate unplugged getaway or you crave the fun and excitement of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to search through hundreds of websites to find the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our professional customer service experts are available 24/7.

Can I go on vacation to Chicago Theatre at this time?

Find out all the info that’s important relating to quarantine policies and travel restrictions ahead of your flight to Chicago Theatre. Our Covid-19 Travel Advisor is full of advice to help make your trip as smooth and carefree as possible.

Top Chicago Theatre hotel deals

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $138

CA $162 total

includes taxes & fees

23 Mar - 24 Mar

Stay at this 4-star 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

L7 Chicago by LOTTE

225 N Wabash Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $212

CA $248 total

includes taxes & fees

23 Mar - 24 Mar

Book a stay at this boutique hotel in Chicago. 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 Chicago Riverwalk and Millennium Park are located nearby.

Pet-friendly

Free WiFi

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $164

CA $193 total

includes taxes & fees

23 Mar - 24 Mar

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Soldier Field are located nearby.

Free WiFi

Restaurant

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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.