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.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star 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.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 15 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Top Hotel Deals
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 ...
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 ...
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 ...
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive, Tinley Park, IL
15.72 km from city center
Stay at this 3.5-star business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
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 ...
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 ...
Super 8 by Wyndham South Holland
17225 Halsted St, South Holland, IL
5.13 km from city center
Book a stay at this business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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. ...
Extended Stay America Suites Chicago Midway
7524 State Rd, Bedford Park, Chicago, IL
26.67 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 helpful staff in our reviews. ...
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 SeatGeek Stadium and Lake Katherine Nature Center are ...
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 ...
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.
Tue, Jun 24 - Tue, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$107 Roundtrip, found 6 days ago
$107
Roundtrip
found 6 days ago
Mon, Jun 23 - Mon, Jun 30
DEN
Denver Intl.
MDW
Midway Intl.
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Thu, Aug 28 - Sun, Aug 31
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Fri, Jun 27 - Fri, Jul 4
IAH
George Bush Intercontinental
MDW
Midway Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Best points of interest in Glenwood
- Lake Michigan Vacations
- Indiana Dunes National Park Vacations
- University of Chicago Vacations
- State Street Vacations
- Rate Field Vacations
- Chicago Museum of Science and Industry Vacations
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