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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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Save 100% on your flight
Price was $830, price is now $553 per person
$553
per person
Jul 16 - Jul 20
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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,043, price is now $648 per person
$648
per person
Jun 24 - Jun 27
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 bars/lounges. 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 Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,146, price is now $721 per person
$721
per person
Jul 16 - Jul 20
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 $1,106, price is now $704 per person
$704
per person
Jun 24 - Jun 27
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.
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 $1,580, price is now $1,014 per person
$1,014
per person
Jun 17 - Jun 21
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,319, price is now $858 per person
$858
per person
Jul 23 - Jul 26
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $2,429, price is now $1,664 per person
$1,664
per person
Jun 17 - Jun 24
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,916, price is now $1,326 per person
$1,326
per person
Jun 17 - Jun 21
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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Glenwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,043, price is now $648 per person
$648
per person
Jun 24 - Jun 27
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 $1,327, price is now $766 per person
$766
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,146, price is now $721 per person
$721
per person
Jul 16 - Jul 20
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 $1,106, price is now $704 per person
$704
per person
Jun 24 - Jun 27
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,345, price is now $702 per person
$702
per person
Jul 22 - Jul 27
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,475, price is now $769 per person
$769
per person
Jul 22 - Jul 27
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,754, price is now $1,032 per person
$1,032
per person
Jun 17 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,677, price is now $992 per person
$992
per person
Jun 17 - Jun 23
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
Tue, Jun 9 - Wed, Jun 17
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$66 Roundtrip, found 2 hours ago
$66
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jun 17, priced at $66 found 2 hours ago
Delta
Wed, Jul 1 - Wed, Jul 22
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Jul 22, priced at $147 found 4 days ago
Delta
Tue, Jun 16 - Wed, Jul 1
IAH
George Bush Intercontinental
MDW
Midway Intl.
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Jun 16 from George Bush Intercontinental to Midway Intl., returning Wed, Jul 1, priced at $197 found 12 hours ago
Delta
Tue, Jun 9 - Wed, Jun 17
MCO
Orlando Intl.
MDW
Midway Intl.
$201 Roundtrip, found 8 hours ago
$201
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Jun 9 from Orlando Intl. to Midway Intl., returning Wed, Jun 17, priced at $201 found 8 hours ago