Glenwood Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave, Bridgeview, IL
25.82 km from city center
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. ...
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave, Oak Lawn, IL
23 km from city center
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave, Chicago, IL
28.24 km from city center
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 ...
Courtyard by Marriott Chicago Midway Airport

Courtyard by Marriott Chicago Midway Airport

3 out of 5
6610 S Cicero Ave, Chicago, IL
28.16 km from city center
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave, Chicago, IL
28.04 km from city center
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 ...
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

2.5 out of 5
6500 S Cicero Ave, Chicago, IL
28.28 km from city center
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 ...
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
18.34 km from city center
Stay at this 4-star beach hotel in East Chicago. Enjoy free parking, 5 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in ...
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
19.1 km from city center
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 ...
Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport

3 out of 5
6550 S Cicero Ave, Chicago, IL
28.17 km from city center
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
12801 South Cicero, Alsip, IL
17.12 km from city center
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 ...
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St, Alsip, IL
17.75 km from city center
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Country Inn & Suites by Radisson, Tinley Park, IL

Country Inn & Suites by Radisson, Tinley Park, IL

3 out of 5
18315 South LaGrange Road, Tinley Park, IL
20.8 km from city center
Stay at this 3-star business-friendly hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Stone Creek Inn

Stone Creek Inn

2.5 out of 5
10600 S Harlem Ave, Worth, IL
23.8 km from city center
Stay at this hotel in Worth. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Lake Katherine Nature Center and Chicago Ridge Shopping ...
Hilton Garden Inn Chicago/Midway Airport

Hilton Garden Inn Chicago/Midway Airport

3 out of 5
6530 S Cicero Ave, Chicago, IL
28.39 km from city center
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St, Hazel Crest, IL
4.67 km from city center
Stay at this 4-star spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe ...
Don't see what you're looking for?
See all available properties in Glenwood
View all properties
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.

Frontier Airlines
Wed, Oct 29 - Wed, Nov 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$76 Roundtrip, found 3 days ago
$76
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Nov 5, priced at $76 found 3 days ago
Frontier Airlines
Fri, Oct 31 - Tue, Nov 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Nov 4, priced at $78 found 1 day ago
Frontier Airlines
Fri, Oct 31 - Sat, Nov 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Nov 1, priced at $83 found 1 day ago
Delta
Sat, Nov 8 - Tue, Nov 11
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 8 from Minneapolis - St. Paul Intl. to Midway Intl., returning Tue, Nov 11, priced at $188 found 2 days ago