Search Deals onGlenwood Vacation Packages
Glenwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
OYO Hotel Edgebrook Chicago North Shore
per person
Aug 15 - Aug 19
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Allstate Arena and Milwaukee Avenue are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Jul 9 - Jul 16
found 1 day ago
Roundtrip flight included
Austin (AUS) 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.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Save 100% on your flight
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago/Midway Airport
Save 100% on your flight
per person
Jul 8 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Aug 15 - Aug 18
found 13 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star 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.
Viceroy Chicago
Save 100% on your flight
per person
Jul 9 - Jul 16
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Glenwood Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Glenwood Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Sep 16 - Tue, Sep 23
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$97 Roundtrip, found 14 hours ago
$97
Roundtrip
found 14 hours ago
Tue, Jul 22 - Wed, Jul 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$109 Roundtrip, found 12 hours ago
$109
Roundtrip
found 12 hours ago
Thu, Jun 12 - Sat, Jun 14
MCO
Orlando Intl.
MDW
Midway Intl.
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Fri, Aug 8 - Mon, Aug 11
IAH
George Bush Intercontinental
MDW
Midway Intl.
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
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