Glenwood Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Glenwood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
Save 100% on your flight
Price was $561, price is now $374 per person
$374
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,770, price is now $788 per person
$788
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Downtown Chicago
Price was $1,617, price is now $889 per person
$889
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,061, price is now $1,199 per person
$1,199
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 5-star 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.
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
Price was $966, price is now $632 per person
$632
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. 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 Clark Street Beach and Halim Time & Glass Museum are located nearby.
La Banque Hotel
Save 100% on your flight
Price was $778, price is now $518 per person
$518
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Top Hotel Deals
Hilton Chicago/Oak Lawn
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 ...
Hyatt Place Chicago Midway Airport
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 ...
Hampton Inn by Hilton Chicago-Midway Airport
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 ...
Sleep Inn Midway Airport Bedford Park
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 ...
Motel 6 Bridgeview, IL
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. ...
Baymont by Wyndham Chicago/Alsip
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 ...
Motel 6 - Chicago, IL
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 ...
Country Inn & Suites by Radisson, Tinley Park, IL
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 ...
Quality Inn & Suites Orland Park - Chicago
8800 W 159th St, Orland Park, IL
20.45 km from city center
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Wind Creek Southland Casino and Hotel
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 ...
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd., East Chicago, IN
18.34 km from city center
Stay at this 4-star beach hotel in East Chicago. Enjoy 5 restaurants, a marina, and a casino. Our guests praise the helpful staff and the clean rooms in our ...
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
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 ...
Stone Creek Inn
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 ...
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.
Fri, Oct 24 - Mon, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Tue, Oct 21 - Tue, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Fri, Oct 24 - Mon, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Tue, Nov 18 - Wed, Nov 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$231 Roundtrip, found 6 days ago
$231
Roundtrip
found 6 days ago