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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $810, price is now $511 per person
$511
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,660, price is now $996 per person
$996
per person
Aug 13 - Aug 17
found 20 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,534, price is now $932 per person
$932
per person
Jul 10 - Jul 15
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 $1,097, price is now $690 per person
$690
per person
Aug 20 - Aug 23
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,016, price is now $644 per person
$644
per person
Aug 26 - Aug 29
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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,635, price is now $1,070 per person
$1,070
per person
Jul 10 - Jul 15
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,078, price is now $718 per person
$718
per person
Aug 20 - Aug 23
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 rooftop terrace, 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 Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $986, price is now $661 per person
$661
per person
Aug 20 - Aug 23
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.

Glenwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $810, price is now $511 per person
$511
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,660, price is now $996 per person
$996
per person
Aug 13 - Aug 17
found 20 hours 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 $1,221, price is now $757 per person
$757
per person
Aug 19 - Aug 23
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 $1,097, price is now $690 per person
$690
per person
Aug 20 - Aug 23
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,418, price is now $853 per person
$853
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,596, price is now $874 per person
$874
per person
Aug 3 - Aug 10
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 $1,880, price is now $1,044 per person
$1,044
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,672, price is now $1,010 per person
$1,010
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Salt Lake City (SLC) 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, Jul 7 - Wed, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$111 Roundtrip, found 1 hour ago
$111
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jul 15, priced at $111 found 1 hour ago
Delta
Tue, Jun 30 - Fri, Jul 3
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 30 from Minneapolis - St. Paul Intl. to Midway Intl., returning Fri, Jul 3, priced at $140 found 3 days ago
Delta
Tue, Sep 1 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Sep 8, priced at $217 found 6 days ago
Delta
Tue, Oct 13 - Wed, Oct 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Delta flight, departing Tue, Oct 13 from Los Angeles Intl. to Midway Intl., returning Wed, Oct 21, priced at $217 just found