Search Deals onThe Loop Vacation Packages
The Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Save 100% on your flight
Price was $747, price is now $540 per person
$540
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,210, price is now $1,427 per person
$1,427
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,165, price is now $771 per person
$771
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,139, price is now $763 per person
$763
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,934, price is now $1,321 per person
$1,321
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was $1,141, price is now $805 per person
$805
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,201, price is now $867 per person
$867
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago - River North
Downtown Chicago
Price was $935, price is now $685 per person
$685
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
citizenM Chicago Downtown
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 ...
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
Save an average of 15% on thousands of hotels when you're signed in
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
River Hotel
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Hilton Chicago
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
Club Quarters Hotel, Central Loop, Chicago
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 ...
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, Sep 30 - Wed, Oct 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Thu, Oct 16 - Mon, Oct 20
LAX
Los Angeles Intl.
MDW
Midway Intl.
$178 Roundtrip, found 7 hours ago
$178
Roundtrip
found 7 hours ago
Mon, Sep 22 - Sat, Oct 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$855 Roundtrip, found 7 hours ago
$855
Roundtrip
found 7 hours ago
Wed, Nov 5 - Mon, Nov 24
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 7 hours ago
$999
Roundtrip
found 7 hours ago
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