
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.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 23
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
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 bar and the helpful staff 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
per person
Sep 19 - Sep 23
found 7 hours ago
Roundtrip flight included
New York (LGA) 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.

Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 23
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

citizenM Chicago Downtown
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 23
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 23
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Stay at this 4-star 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.

Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 23
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa 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 Millennium Park and Chicago Riverwalk are located nearby.
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citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
0.62 km from Theatre District
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
0.21 km from Theatre District
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...

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 bar ...

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 ...

Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
0.35 km from Theatre District
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...

Pendry Chicago
230 North Michigan Avenue, Chicago, IL
0.61 km from Theatre District
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...

Arlo Chicago
168 N Michigan Avenue, Chicago, IL
0.47 km from Theatre District
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our ...

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. ...

Hilton Garden Inn Chicago Downtown Riverwalk
66 East Wacker Place, Chicago, IL
0.6 km from Theatre District
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our ...

Hyatt Centric The Loop Chicago
100 W. Monroe St, Chicago, IL
0.25 km from Theatre District
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a rooftop terrace, 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
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...

Kimpton Gray Hotel by IHG
122 West Monroe Street, Chicago, IL
0.29 km from Theatre District
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise 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.

Sat, Aug 30 - Tue, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago

Sat, Aug 30 - Tue, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$144 Roundtrip, found 5 days ago
$144
Roundtrip
found 5 days ago

Sat, Aug 30 - Tue, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago

Sat, Aug 30 - Tue, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago

Tue, Sep 2 - Wed, Sep 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Best points of interest in Chicago
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