
Theatre District Vacation Packages for 2026
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Theatre District Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,241, price is now $833 per person
$833
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet 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.
We had a wonderful stay! The hotel was very clean, and the staff who checked us in and out were incredibly kind and welcoming. The location was perfect—we were able to walk everywhere we wanted to go, which made our trip so convenient. I would definitely stay here again!
Reviewed on Jul 2, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,646, price is now $975 per person
$975
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
Columbia (CAE) 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.
Our first time visiting Chicago and the hotel was hands down the best. Located in downtown Chicago, which made everything pretty much walking distance. The complimentary breakfast (buffet style) was great with many options to choose from. Staff were amazing and were kind enough to accommodate us with an early check- in (with an extra cost since we arrived in at 7:30am).
My one and only complaint was that it would have been nice to have our breakfast included with the early check in since we paid $100 for that. We were told that we were welcome to go have breakfast but at an additional cost which was $25/adult and $12/child. We paid it since we had just come in from a long flight and wanted some food. Overall a great experience, we definitely plan on staying again at our next trip to Chicago.
Reviewed on Jul 3, 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,779, price is now $1,143 per person
$1,143
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
Columbia (CAE) 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.
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,721, price is now $1,154 per person
$1,154
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Excellente
Reviewed on Jul 1, 2026

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,301, price is now $924 per person
$924
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
No one answers the phone at the spa.
Bathtub clogged, engineering called and I was simply told the tub was not clogged so had to shower with water up to my ankles.
They do have a bar but it’s not well stocked.
The blinds in the room don’t hang properly, they’re wonky, and have to be moved by chain.
This is not a 4 star hotel. It’s not 3 either. Save your money and stay at a nice Hampton or Courtyard instead. This is a gross place, terrible staff.
Reviewed on Jul 2, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,543, price is now $1,104 per person
$1,104
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
Columbia (CAE) 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 clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
10/10
Reviewed on Jul 3, 2026
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Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
0.21 km from Theatre District
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

Arlo Chicago
168 N Michigan Avenue Chicago IL
0.47 km from Theatre District
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
0.45 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful ...

L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
0.55 km from Theatre District
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...

Central Loop Hotel
111 West Adams Street Chicago IL
0.35 km from Theatre District
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...

Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
0.37 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...

citizenM Chicago Downtown
80 East Wacker Place Chicago IL
0.62 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...

Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
0.19 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...

theWit Chicago, a Hilton Hotel
201 N State Street Chicago IL
0.45 km from Theatre District
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 ...

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
0.44 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...

Sports Illustrated Resorts Chicago
203 N Wabash Ave Chicago IL
0.49 km from Theatre District
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...

Hyatt Centric The Loop Chicago
100 W. Monroe St Chicago IL
0.23 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...

Cambria Hotel Chicago Loop - Theatre District
32 West Randolph Street Chicago IL
0.26 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the ...
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See all available properties in Theatre District
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 19 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago

Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 12 hours ago
$238
Roundtrip
found 12 hours ago

Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$248 Roundtrip, found 12 hours ago
$248
Roundtrip
found 12 hours ago

Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 12 hours ago
$277
Roundtrip
found 12 hours ago

Tue, Aug 25 - Tue, Sep 8
LAX
Los Angeles Intl.
MDW
Midway Intl.
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago

