Theatre District Vacation Packages for 2025

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Theatre District Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 23
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 23
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 18 - Aug 23
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) 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

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 23
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) 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.

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 23
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this 4-star 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.

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 23
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.

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Top Hotel Deals

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
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

Palmer House a Hilton Hotel

4 out of 5
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 ...
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave, Chicago, IL
0.22 km from Theatre District
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the ...
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
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

Arlo Chicago

4 out of 5
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 ...
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
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 ...
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
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 ...
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street, Chicago, IL
0.35 km from Theatre District
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
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 ...
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
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. ...
Pendry Chicago

Pendry Chicago

4.5 out of 5
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 ...
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
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 ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
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), 24-hour room service, and a 24-hour fitness center. Our guests praise the ...
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
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 ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
0.86 km from Theatre District
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 ...
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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.

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.

Spirit Airlines
Wed, Aug 20 - Sun, Aug 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 6 days ago
$130
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Aug 20 from Los Angeles Intl. to O'Hare Intl., returning Sun, Aug 24, priced at $130 found 6 days ago
Frontier Airlines
Thu, Aug 21 - Sat, Aug 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $174 found 6 days ago
Hawaiian Airlines
Tue, Aug 26 - Tue, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 19 hours ago
$216
Roundtrip
found 19 hours ago
Select Hawaiian Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 2, priced at $216 found 19 hours ago
Frontier Airlines
Tue, Aug 19 - Sat, Aug 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Aug 19 from Los Angeles Intl. to Midway Intl., returning Sat, Aug 23, priced at $240 found 5 days ago