Theatre District Vacation Packages
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Top Holiday Package Deals in Theatre District
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip.
The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.
Reviewed on Jul. 21, 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The front desk staff was stellar! I cannot remember her name but she was training a new woman. She was amazing. They both were. She answered ALL of my many questions with grace and kindness. She was professional and helpful with recommendations for city dining as well. Thank you! I will be visiting again!
Reviewed on Jul. 25, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Excellent stay, food court right downstairs, flyover onsite, childrens museum, pier at night is amazing
Reviewed on Jul. 25, 2025
Where to stay in Theatre District
Find the best Theatre District areas and neighborhoods for the activities you enjoy most. Learn more about Theatre District
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Theatre District Hotel Deals
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Aug 26 to Aug 27
CA $213
CA $251 total
Aug 26 - Aug 27
includes taxes & fees
9.2/10 Wonderful! (3,448 reviews)
"It was a great day in Chicago. I love the location and amenities. It was very walking distance to all the places we wanted to go. The rooms were small, but a good size were two of us and we just needed it for the nights to sleep. The design was very unique and modern, which was nice. Definitely recommend ..."
Reviewed on Jul. 25, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $238 per night from Aug 22 to Aug 23
CA $238
CA $313 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,796 reviews)
"Palmer House is an excellent location. Plenty of restaurants, parks and shopping are nearby. The subway is just outside one of the exits. The hotel is huge, with exits to four different streets. A bar, restaurant, coffee shop, Starbucks and a sweet shop all convenient in the hotel area. I marked ..."
Reviewed on Jul. 21, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Aug 10 to Aug 11
CA $215
CA $296 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,899 reviews)
Price is right for an overnight stay
"Friendly and nice hotel for the price. The rooms are a little small, since it's an older hotel. However, it's quiet and in a good location."
Reviewed on Jul. 24, 2025
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.
Frequently asked questions
Discover the most popular places to visit in Theatre District
Chicago Theatre
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
Richard J. Daley Center
Richard J. Daley Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or visit the notable monuments in this vibrant area.
CIBC Theatre
You can get tickets for a performance at CIBC Theatre on your trip to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Things to do
Chicago: Architecture Boat Tour with Drinks
CA $57
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
86% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.