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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $929, price is now $624 per person
$624
per person
Jul 2 - Jul 6
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant 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 $1,142, price is now $740 per person
$740
per person
Jul 2 - Jul 6
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $3,235, price is now $2,229 per person
$2,229
per person
Jul 9 - Jul 16
found 11 hours ago
Roundtrip flight included
Spokane (GEG) to Chicago (ORD)
Book a stay at this 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,010, price is now $697 per person
$697
per person
Jul 2 - Jul 6
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,509, price is now $1,069 per person
$1,069
per person
Jul 2 - Jul 6
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Warwick Allerton - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,550, price is now $1,102 per person
$1,102
per person
Jul 9 - Jul 16
found 13 hours ago
Roundtrip flight included
Spokane (GEG) to Chicago (ORD)
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, 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.
Top Hotel Deals
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 ...
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 ...
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
17.87 km from city center
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 ...
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 ...
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 ...
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. ...
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. ...
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
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 ...
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 ...
Fairfield Inn and Suites by Marriott Chicago Midway Airport
6630 S Cicero Ave Chicago IL
28.14 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 helpful staff and ...
Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond
7720 Corinne Dr Hammond IN
12.01 km from city center
Book a stay at this business-friendly hotel in Hammond. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
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 ...
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.
Wed, Sep 16 - Tue, Sep 22
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$76 Roundtrip, found 5 days ago
$76
Roundtrip
found 5 days ago
Tue, Sep 15 - Tue, Sep 22
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$87 Roundtrip, found 5 days ago
$87
Roundtrip
found 5 days ago
Tue, Jun 23 - Wed, Jun 24
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Tue, Jun 23 - Wed, Jun 24
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago