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 $310, price is now $215 per person
$215
per person
Feb 5 - Feb 9
found 2 days ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was $559, price is now $375 per person
$375
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
Motel 6 - Chicago, IL
Washington Heights
Price was $438, price is now $322 per person
$322
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located nearby.
Millennium Knickerbocker Chicago
Downtown Chicago
Price was $513, price is now $382 per person
$382
per person
Jan 16 - Jan 23
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, a 24-hour fitness center, 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.
Dorothy's
Lakeview
Price was $367, price is now $279 per person
$279
per person
Jan 16 - Jan 23
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
The Drake
Downtown Chicago
Price was $460, price is now $353 per person
$353
per person
Jan 27 - Feb 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a fitness center. 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
Price was $594, price is now $401 per person
$401
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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
Save 100% on your flight
Price was $984, price is now $679 per person
$679
per person
Feb 5 - Feb 9
found 2 days ago
Roundtrip flight included
Dallas (DFW) 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
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 ...
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr 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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
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 ...
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 12 - Mon, Feb 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 9 hours ago
$150
Roundtrip
found 9 hours ago
Thu, Jan 8 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$194 Roundtrip, found 9 hours ago
$194
Roundtrip
found 9 hours ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$401 Roundtrip, found 5 days ago
$401
Roundtrip
found 5 days ago
Thu, May 7 - Mon, May 18
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,170 Roundtrip, found 6 hours ago
$1,170
Roundtrip
found 6 hours ago
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