Search Deals onThe Loop Vacation Packages
The Loop Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Dorothy's
Lakeview
Price was $408, price is now $328 per person
$328
per person
Dec 15 - Dec 19
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this B&B in Chicago. Enjoy free breakfast, free WiFi, and housekeeping. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Price was $877, price is now $665 per person
$665
per person
Dec 18 - Dec 22
found 1 day 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.
Park Hyatt Chicago
Downtown Chicago
Price was $4,709, price is now $3,586 per person
$3,586
per person
Dec 6 - Dec 12
found 6 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Villa Christina
Greater Grand Crossing
Price was $1,119, price is now $880 per person
$880
per person
Dec 3 - Dec 7
found 14 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Wintrust Arena and Obama Presidential Center are located nearby.
Chez Hotel Arlington Heights
Price was $440, price is now $353 per person
$353
per person
Dec 4 - Dec 8
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Allstate Arena are located nearby.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was $2,438, price is now $587 per person
$587
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (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 Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,090, price is now $691 per person
$691
per person
Dec 11 - Dec 17
found 10 hours 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,380, price is now $981 per person
$981
per person
Dec 11 - Dec 17
found 12 hours 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 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center 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 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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
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 ...
Sports Illustrated Resorts Chicago
203 N Wabash Ave Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). 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 ...
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.
Mon, Dec 7 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 2 hours ago
$164
Roundtrip
found 2 hours ago
Wed, Nov 25 - Wed, Dec 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$259 Roundtrip, found 2 hours ago
$259
Roundtrip
found 2 hours ago
Tue, Dec 29 - Thu, Dec 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 1 hour ago
$263
Roundtrip
found 1 hour ago
Fri, Nov 13 - Fri, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,125 Roundtrip, found 23 hours ago
$1,125
Roundtrip
found 23 hours ago
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