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Theatre District Vacation Packages

Theatre District Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel

Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel

3 out of 5
O'Hare
per person
Feb 23 - Feb 28
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Wolff's Flea Market and Allstate Arena are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 9 - Feb 15
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park are located nearby.
The Drake

The Drake

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 14 - Feb 19
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
per person
Feb 23 - Feb 28
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Skokie. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions North Shore Center for the Performing Arts and Adagio Teas are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Chicago Marriott Oak Brook

Chicago Marriott Oak Brook

3.5 out of 5
per person
Feb 23 - Feb 28
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Oak Brook. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
SpringHill Suites Chicago O'Hare by Marriott

SpringHill Suites Chicago O'Hare by Marriott

3 out of 5
Norwood Park
per person
Feb 23 - Feb 28
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Rosemont Theatre and Rivers Casino are located nearby.

3-4 Night Vacations in Theatre District

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Theatre District

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 14 - Feb 19
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 9 - Feb 15
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to Chicago (ORD)

Cheap Hotel Deals in Theatre District

Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue, Chicago, IL
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 ...
Pendry Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
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 ...
Club Quarters Hotel, Central Loop, Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
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 ...
Palmer House a Hilton Hotel
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citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
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 ...
citizenM Chicago Downtown
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave, Chicago, IL
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 ...
Silversmith Hotel Chicago Downtown
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
100 W. Monroe St, Chicago, IL
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 ...
Hyatt Centric The Loop Chicago
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
203 N Wabash Ave, Chicago, IL
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. ...
Virgin Hotels Chicago
Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
66 East Wacker Place, Chicago, IL
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 ...
Hilton Garden Inn Chicago Downtown Riverwalk
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Mar 17 - Tue, Mar 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Mar 17 from Los Angeles Intl. to Midway Intl., returning Tue, Mar 18, priced at $115 just found
Frontier Airlines
Sat, Feb 8 - Mon, Feb 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 23 hours ago
$120
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Feb 8 from Los Angeles Intl. to O'Hare Intl., returning Mon, Feb 10, priced at $120 found 23 hours ago
Scandinavian Airlines
Sat, Mar 22 - Mon, Mar 31
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$537 Roundtrip, found 1 day ago
$537
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Sat, Mar 22 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Mon, Mar 31, priced at $537 found 1 day ago
American Airlines
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$937 Roundtrip, found 1 day ago
$937
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 25 from Pudong Intl. to O'Hare Intl., returning Sun, Mar 2, priced at $937 found 1 day ago