Search Deals onGlenwood Vacation Packages
Glenwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $407, price is now $201 per person
$201
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hilton Grand Vacations Club Chicago Magnificent Mile
Price was $452, price is now $212 per person
$212
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Art Villa
Save 100% on your flight
Price was $964, price is now $456 per person
$456
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.

Pendry Chicago
Price was $605, price is now $289 per person
$289
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Emily Hotel
Price was $1,029, price is now $527 per person
$527
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.

Level Chicago – Old Town
Price was $634, price is now $325 per person
$325
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.

theWit Chicago, a Hilton Hotel
Save 100% on your flight
Price was $419, price is now $221 per person
$221
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Blackstone, Autograph Collection
Save 100% on your flight
Price was $467, price is now $248 per person
$248
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park 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.

Thu, Nov 27 - Wed, Dec 31
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$64 Roundtrip, found 4 days ago
$64
Roundtrip
found 4 days ago

Thu, Nov 6 - Sat, Nov 8
MCO
Orlando Intl.
MDW
Midway Intl.
$69 Roundtrip, found 3 days ago
$69
Roundtrip
found 3 days ago

Fri, Dec 12 - Sun, Dec 14
IAH
George Bush Intercontinental
MDW
Midway Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago

Mon, Dec 8 - Mon, Dec 15
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$140 Roundtrip, found 21 hours ago
$140
Roundtrip
found 21 hours ago
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