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Glenwood Vacation Packages

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Glenwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $739, price is now $489 per person
$489
per person
Jul 18 - Jul 21
found 12 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,415, price is now $892 per person
$892
per person
Jul 28 - Aug 1
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,231, price is now $789 per person
$789
per person
Jul 10 - Jul 14
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

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $864, price is now $577 per person
$577
per person
Aug 5 - Aug 8
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,262, price is now $854 per person
$854
per person
Aug 13 - Aug 16
found 23 hours 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,052, price is now $727 per person
$727
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $877, price is now $608 per person
$608
per person
Aug 5 - Aug 8
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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,910, price is now $1,327 per person
$1,327
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise 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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $739, price is now $489 per person
$489
per person
Jul 18 - Jul 21
found 12 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,415, price is now $892 per person
$892
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,231, price is now $789 per person
$789
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $864, price is now $577 per person
$577
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Glenwood Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,589, price is now $957 per person
$957
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,177, price is now $1,210 per person
$1,210
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,451, price is now $1,514 per person
$1,514
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,045, price is now $1,279 per person
$1,279
per person
Jul 28 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Jun 13 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 13 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 16, priced at $137 found 1 day ago
Delta
Wed, Jul 1 - Wed, Jul 22
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jul 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Jul 22, priced at $137 found 6 days ago
Delta
Tue, Jun 23 - Wed, Jun 24
IAH
George Bush Intercontinental
MDW
Midway Intl.
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Jun 23 from George Bush Intercontinental to Midway Intl., returning Wed, Jun 24, priced at $197 found 10 hours ago
Delta
Tue, Aug 4 - Wed, Aug 12
MCO
Orlando Intl.
MDW
Midway Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Aug 4 from Orlando Intl. to Midway Intl., returning Wed, Aug 12, priced at $197 found 4 hours ago