Theatre District Vacation Packages for 2026
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.
Sports Illustrated Resorts Chicago
Downtown Chicago
$632
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$818
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,203
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
This is an elegant and high class facility with warm service and hospitality stuff
Centrally located on North River north bank.
The room is big and spacious overlooking the river.
We loved our stay.
The concierge gave us a great tips and services
Recommend by all means.
Reviewed on Oct 2, 2026
The Talbott, Autograph Collection
Downtown Chicago
$711
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
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 clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North
Downtown Chicago
$1,013
per person
Nov 5 - Nov 10
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
$1,016
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Fantastic as always. Highly recommend
Reviewed on Oct 1, 2026
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See all available trips from Columbus to Theatre District
View all tripsTop Hotel Deals
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
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
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
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 ...
Sports Illustrated Resorts Chicago
203 N Wabash Ave Chicago IL
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 ...
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
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 ...
Arlo Chicago
168 N Michigan Avenue Chicago IL
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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
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 ...
Hyatt Centric The Loop Chicago
100 W. Monroe St Chicago IL
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 ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
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 ...
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
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
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 ...
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
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 ...
Cambria Hotel Chicago Loop - Theatre District
32 West Randolph Street Chicago IL
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 ...
LIVN - Millennium Park Downtown Chicago
19 South Wabash Avenue Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Millennium Park and Chicago Riverwalk are located ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
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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, Oct 21 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88
Roundtrip
found 2 days ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 1 hour ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 1 hour ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 1 hour ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$203
Roundtrip
found 2 days ago
Best points of interest in Chicago
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