Search Deals onThe Loop Vacation Packages
The Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $968, price is now $610 per person
$610
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,362, price is now $835 per person
$835
per person
Jun 10 - Jun 14
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 Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,219, price is now $780 per person
$780
per person
Jun 10 - Jun 14
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,599, price is now $1,028 per person
$1,028
per person
Jun 18 - Jun 22
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,167, price is now $755 per person
$755
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,215, price is now $790 per person
$790
per person
Jun 10 - Jun 14
found 22 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 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,299, price is now $862 per person
$862
per person
Jun 10 - Jun 14
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,788, price is now $1,215 per person
$1,215
per person
Jun 10 - Jun 14
found 22 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.
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 ...
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 ...
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 ...
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 ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
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 ...
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 ...
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 ...
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, May 28 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 14 hours ago
$168
Roundtrip
found 14 hours ago
Tue, May 19 - Thu, May 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$246 Roundtrip, found 14 hours ago
$246
Roundtrip
found 14 hours ago
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$315 Roundtrip, found 6 days ago
$315
Roundtrip
found 6 days ago
Wed, Jul 8 - Wed, Jul 22
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$924 Roundtrip, found 16 hours ago
$924
Roundtrip
found 16 hours ago
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