Search Deals onThe Loop Vacation Packages
The Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $878, price is now $601 per person
$601
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $2,133, price is now $1,272 per person
$1,272
per person
Aug 5 - Aug 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,311, price is now $858 per person
$858
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,472, price is now $982 per person
$982
per person
Aug 20 - Aug 25
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,454, price is now $976 per person
$976
per person
Aug 6 - Aug 10
found 1 day 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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Ashburn
Save 100% on your flight
Price was $1,241, price is now $843 per person
$843
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and room service. Popular attractions SeatGeek Stadium and Wintrust Sports Complex are located nearby.
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,026, price is now $717 per person
$717
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,236, price is now $875 per person
$875
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
3-4 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 ...
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 ...
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
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. ...
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 ...
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.
Tue, Aug 25 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 10 hours ago
$216
Roundtrip
found 10 hours ago
Tue, Aug 18 - Sat, Sep 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$269 Roundtrip, just found
$269
Roundtrip
just found
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$419 Roundtrip, found 1 day ago
$419
Roundtrip
found 1 day ago
Sat, Jul 4 - Sat, Jul 18
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$728 Roundtrip, found 1 day ago
$728
Roundtrip
found 1 day ago
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