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 $324, price is now $231 per person
$231
per person
Jan 22 - Jan 26
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.
Millennium Knickerbocker Chicago
Downtown Chicago
Price was $378, price is now $256 per person
$256
per person
Jan 27 - Feb 1
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,281, price is now $836 per person
$836
per person
Feb 12 - Feb 16
found 1 day 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.
citizenM Chicago Downtown
Downtown Chicago
Save 100% on your flight
Price was $436, price is now $294 per person
$294
per person
Jan 22 - Jan 26
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, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $543, price is now $379 per person
$379
per person
Jan 22 - Jan 26
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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $463, price is now $323 per person
$323
per person
Jan 22 - Jan 26
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.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $487, price is now $343 per person
$343
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $475, price is now $338 per person
$338
per person
Jan 22 - Jan 26
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 Millennium Park and Soldier Field 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, Dec 25 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Mon, Jan 12 - Wed, Jan 14
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$382 Roundtrip, found 7 hours ago
$382
Roundtrip
found 7 hours ago
Thu, May 7 - Mon, May 18
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,170 Roundtrip, found 20 hours ago
$1,170
Roundtrip
found 20 hours ago
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