Search Deals onGlenwood Vacation Packages
Glenwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Price was $431, price is now $279 per person
$279
per person
Dec 3 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.
Hotel Riu Plaza Chicago
Price was $683, price is now $392 per person
$392
per person
Jan 22 - Jan 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.
Great location, nice rooms, nice rooftop bar and large breakfast buffet included.
Reviewed on Oct 28, 2026
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Price was $1,110, price is now $685 per person
$685
per person
Dec 16 - Dec 23
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $492, price is now $308 per person
$308
per person
Dec 4 - Dec 6
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.
Super clean. Super views. Super amenities. Will stay again.
Reviewed on Oct 26, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $617, price is now $430 per person
$430
per person
Jan 1 - Jan 6
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 stay was everything I love the view and peaceful. Thank you
Reviewed on Oct 26, 2026
Villa Christina
Price was $744, price is now $519 per person
$519
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Rate Field and Wintrust Arena are located nearby.
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.
Reviewed on Aug 4, 2026
The Emily Hotel
Save 100% on your flight
Price was $864, price is now $605 per person
$605
per person
Jan 1 - Jan 6
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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Price was $777, price is now $547 per person
$547
per person
Jan 22 - Jan 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.
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, Dec 5 - Sat, Dec 12
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$128 Roundtrip, just found
$128
Roundtrip
just found
Fri, Jan 15 - Tue, Jan 19
MCO
Orlando Intl.
MDW
Midway Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Thu, Nov 19 - Thu, Nov 26
DEN
Denver Intl.
MDW
Midway Intl.
$192 Roundtrip, found 10 hours ago
$192
Roundtrip
found 10 hours ago
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