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 Saint Clair- Magnificent Mile
Downtown Chicago
$584
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
This place showed up in the options for 18+ check-in allowed, but it turns out it wasn't. That might be my fault on my part but it should be made clearer through Expedia. Staff were okay; some were a little rude but not overly. The hotel room itself was clean, and there were no problems in that regard. The stay was expensive due to travelling during Lollapalooza and would most likely be cheaper at any other time. Overall 3/5. Not worth the money, but would be much more worth it if it was cheaper.
Reviewed on Aug 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$909
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$1,099
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Great beautiful rooms. Nice beds
Reviewed on Aug 7, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$1,126
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$742
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
$975
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Top Hotel Deals
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. ...
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 ...
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 - 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 Abbott Park and Martin Luther King Drive are located ...
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. ...
William Tell Hotel MOD Collection by Sonesta
6201 Joliet Rd Countryside IL
Book a stay at this business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the clean ...
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 ...
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe ...
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 ...
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 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. ...
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 ...
Hyatt Place Chicago Midway Airport
6550 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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 ...
Luxe Inn and Suites
1335 E. SIBLEY BLVD. Dolton IL
Stay at this motel in Dolton. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Veterans Memorial Park and River Oaks Center are located ...
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.
Thu, Sep 3 - Tue, Sep 8
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$157
Roundtrip
found 2 days ago
Thu, Sep 10 - Sat, Sep 12
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$166
Roundtrip
found 3 days ago
Tue, Nov 3 - Mon, Nov 9
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217
Roundtrip
found 9 hours ago
Thu, Nov 5 - Sun, Nov 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$234
Roundtrip
found 9 hours ago
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