Search Deals onThe Loop Vacation Packages
The Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $397, price is now $298 per person
$298
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was $813, price is now $652 per person
$652
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,293, price is now $845 per person
$845
per person
Mar 13 - Mar 17
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,554, price is now $1,148 per person
$1,148
per person
Mar 13 - Mar 17
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $797, price is now $617 per person
$617
per person
Mar 13 - Mar 17
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,187, price is now $936 per person
$936
per person
Mar 21 - Mar 25
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $599, price is now $473 per person
$473
per person
Mar 7 - Mar 11
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Downtown Chicago
Save 100% on your flight
Price was $509, price is now $405 per person
$405
per person
Mar 7 - Mar 11
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this aparthotel in Chicago. Enjoy a fitness center, concierge services, and premium bedding. Our guests praise the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
3-4 Night Vacations in The Loop
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in The Loop
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in The Loop
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Save an average of 15% on thousands of hotels when you're signed in
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 ...
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Pendry Chicago
230 North Michigan Avenue Chicago IL
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 ...
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.
Thu, Feb 26 - Tue, Mar 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$133 Roundtrip, found 4 hours ago
$133
Roundtrip
found 4 hours ago
Thu, Feb 12 - Tue, Feb 24
LAX
Los Angeles Intl.
MDW
Midway Intl.
$194 Roundtrip, found 4 hours ago
$194
Roundtrip
found 4 hours ago
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$242 Roundtrip, found 4 hours ago
$242
Roundtrip
found 4 hours ago
Tue, Feb 24 - Tue, Mar 17
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,059 Roundtrip, found 2 days ago
$1,059
Roundtrip
found 2 days ago
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