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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $1,127, price is now $796 per person
$796
per person
Jun 30 - Jul 5
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) 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
Save 100% on your flight
Price was $1,516, price is now $888 per person
$888
per person
Jun 30 - Jul 5
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,363, price is now $914 per person
$914
per person
Jun 30 - Jul 5
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,844, price is now $1,251 per person
$1,251
per person
Jun 30 - Jul 5
found 6 hours ago
Roundtrip flight included
San Antonio (SAT) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,551, price is now $1,054 per person
$1,054
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,673, price is now $1,149 per person
$1,149
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff 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 ...
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
26.71 km from city center
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
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. ...
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
4.67 km from city center
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 ...
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive Tinley Park IL
15.73 km from city center
Book a stay at this business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
Hampton Inn Chicago Orland Park
16176 LaGrange Road Orland Park IL
21.79 km from city center
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
29.32 km from city center
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. ...
Econo Lodge South Holland - Chicago Southland
17301 S Halsted St, Building B South Holland IL
4.99 km from city center
Stay at this hotel in South Holland. Enjoy free WiFi, free parking, and room service. Popular attractions Midwest Carvers Museum and Harvey Public Library are ...
Courtyard by Marriott Chicago Midway Airport
6610 S Cicero Ave Chicago IL
28.16 km from city center
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 ...
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
28.3 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 ...
Wingate by Wyndham Tinley Park
18421 N Creek Drive Tinley Park IL
16.14 km from city center
Stay at this hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hyatt Place Chicago-South/University Medical Center
5225 S Harper Ave Chicago IL
28.67 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff ...
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, Apr 30 - Sat, May 2
MCO
Orlando Intl.
MDW
Midway Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Fri, Apr 24 - Wed, Apr 29
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Sat, Apr 25 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$82 Roundtrip, found 2 days ago
$82
Roundtrip
found 2 days ago
Thu, May 28 - Sun, May 31
DEN
Denver Intl.
MDW
Midway Intl.
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago