Theatre District Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Theatre District Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $523, price is now $328 per person
$328
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $880, price is now $521 per person
$521
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star 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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $595, price is now $363 per person
$363
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $760, price is now $490 per person
$490
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $687, price is now $446 per person
$446
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,383, price is now $905 per person
$905
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
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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 ...
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 ...
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 ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
0.35 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 ...
Hyatt Centric The Loop Chicago
100 W. Monroe St Chicago IL
0.25 km from Theatre District
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff ...
Pendry Chicago
230 North Michigan Avenue Chicago IL
0.61 km from Theatre District
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 ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
0.55 km from Theatre District
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 ...
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. ...
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
0.22 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 ...
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 ...
theWit Chicago, a Hilton Hotel
201 N State Street Chicago IL
0.43 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 ...
Virgin Hotels Chicago
203 N Wabash Ave Chicago IL
0.49 km from Theatre District
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. ...
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 ...
Don't see what you're looking for?
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.
Thu, Dec 4 - Thu, Dec 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 5 days ago
$73
Roundtrip
found 5 days ago
Wed, Dec 3 - Tue, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 2 days ago
$234
Roundtrip
found 2 days ago
Fri, Dec 5 - Sun, Dec 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago