Flossmoor Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Flossmoor Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$543
per person
Nov 1 - Nov 6
found 24 hours 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$686
per person
Nov 1 - Nov 6
found 24 hours 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.
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious
Reviewed on Sep 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,307
per person
Nov 1 - Nov 6
found 1 day 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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$952
per person
Nov 1 - Nov 6
found 24 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.
Great location! Would stay again!
Reviewed on Sep 23, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
$851
per person
Nov 1 - Nov 6
found 1 day 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 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.
This is my new favorite hotel in the city. ❤️
Reviewed on Sep 23, 2026
Stay One Chicago
Downtown Chicago
$1,503
per person
Nov 1 - Nov 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!
Reviewed on Sep 20, 2026
Top Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Motel 6 Bridgeview, IL
9625 S 76th Ave Bridgeview IL
Stay at this motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Book a stay at this luxury resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Ravisloe Country Club and Oak Hill ...
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Book a stay at this beach hotel in East Chicago. Enjoy free parking, 5 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms in ...
Baymont by Wyndham Chicago/Alsip
12801 South Cicero Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
Book a stay at this boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Courtyard by Marriott Chicago Midway Airport
6610 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Harborside International Golf Center and Martin Luther ...
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Best Western Plus Chicagoland - Countryside
6251 Joliet Rd Countryside IL
Stay at this hotel in Countryside. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Motel 6 Hammond, IN - Chicago Area
3840 179th St Hammond IN
Stay at this motel in Hammond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Oct 17 - Tue, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138
Roundtrip
found 6 days ago
Tue, Dec 1 - Fri, Dec 4
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$144
Roundtrip
found 20 hours ago
Thu, Oct 22 - Tue, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$153
Roundtrip
found 6 days ago
Wed, Mar 17 - Tue, Mar 23
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217
Roundtrip
found 4 days ago
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