Search Deals onGlenwood Vacation Packages
Glenwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $626, price is now $387 per person
$387
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Price was $1,263, price is now $638 per person
$638
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
Level Chicago Fulton Market
Price was $1,890, price is now $1,011 per person
$1,011
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,696, price is now $993 per person
$993
per person
Sep 20 - Sep 25
found 1 day 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.
Swissotel - Chicago
Save 100% on your flight
Price was $941, price is now $564 per person
$564
per person
Oct 21 - Oct 24
found 1 day 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.
Beautiful room & View!! Will definitely book again!
Reviewed on Aug 19, 2026
Level Chicago - River North
Save 100% on your flight
Price was $2,127, price is now $1,299 per person
$1,299
per person
Sep 20 - Sep 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. 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
Price was $1,772, price is now $1,098 per person
$1,098
per person
Sep 20 - Sep 25
found 1 day 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.
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $684, price is now $435 per person
$435
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour 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.
Very nice place to stay. Rooms were just a bit on the smaller side.
Reviewed on Aug 19, 2026
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.
Sat, Oct 24 - Tue, Nov 10
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$172 Roundtrip, just found
$172
Roundtrip
just found
Wed, Sep 23 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$181 Roundtrip, just found
$181
Roundtrip
just found
Tue, Sep 1 - Tue, Sep 8
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$182 Roundtrip, found 22 hours ago
$182
Roundtrip
found 22 hours ago
Sat, Oct 24 - Sat, Nov 7
IAH
George Bush Intercontinental
MDW
Midway Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
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