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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $338, price is now $236 per person
$236
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $652, price is now $375 per person
$375
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $316 per person
$316
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $727, price is now $485 per person
$485
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $649, price is now $445 per person
$445
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $482, price is now $336 per person
$336
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a 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.
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 ...
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. ...
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 - 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 ...
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 ...
Courtyard by Marriott Chicago Midway Airport
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 ...
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 ...
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 ...
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 free parking, 5 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in ...
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 ...
DoubleTree by Hilton Chicago - Alsip
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 ...
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 ...
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, Nov 27 - Tue, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, found 6 hours ago
$68
Roundtrip
found 6 hours ago
Thu, Nov 27 - Thu, Dec 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$69 Roundtrip, found 6 hours ago
$69
Roundtrip
found 6 hours ago
Thu, Dec 4 - Mon, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$70 Roundtrip, found 6 hours ago
$70
Roundtrip
found 6 hours ago
Thu, Jan 1 - Tue, Jan 20
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago