Search Deals on
Glenwood Vacation Packages

Build your package with 2 more options

Glenwood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Save 100% on your flight
Price was $682, price is now $399 per person
$399
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $948, price is now $519 per person
$519
per person
Jun 25 - Jun 28
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 $860, price is now $502 per person
$502
per person
Jun 17 - Jun 20
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.
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 $1,030, price is now $636 per person
$636
per person
Jun 17 - Jun 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, 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.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Price was $724, price is now $449 per person
$449
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $672, price is now $421 per person
$421
per person
Jun 17 - Jun 20
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
Price was $1,292, price is now $810 per person
$810
per person
Jul 9 - Jul 13
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $721, price is now $476 per person
$476
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.

Glenwood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $682, price is now $399 per person
$399
per person
Jun 17 - Jun 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 $948, price is now $519 per person
$519
per person
Jun 25 - Jun 28
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 $860, price is now $502 per person
$502
per person
Jun 17 - Jun 20
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 $1,030, price is now $636 per person
$636
per person
Jun 17 - Jun 20
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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,081, price is now $578 per person
$578
per person
Jul 1 - Jul 8
found 22 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 $1,559, price is now $748 per person
$748
per person
Jul 1 - Jul 8
found 22 hours 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 $1,294, price is now $672 per person
$672
per person
Jul 1 - Jul 8
found 22 hours 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 $1,989, price is now $1,149 per person
$1,149
per person
Jul 1 - Jul 8
found 20 hours 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
Wed, Jun 3 - Thu, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jun 3 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Jun 4, priced at $86 found 1 day ago
Delta
Sat, May 23 - Tue, Jun 2
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$161 Roundtrip, found 7 hours ago
$161
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, May 23 from Minneapolis - St. Paul Intl. to Midway Intl., returning Tue, Jun 2, priced at $161 found 7 hours ago
Frontier Airlines
Wed, May 20 - Wed, May 27
IAH
George Bush Intercontinental
MDW
Midway Intl.
$174 Roundtrip, found 19 hours ago
$174
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, May 20 from George Bush Intercontinental to Midway Intl., returning Wed, May 27, priced at $174 found 19 hours ago
Frontier Airlines
Sun, May 24 - Mon, Jun 1
DEN
Denver Intl.
MDW
Midway Intl.
$190 Roundtrip, found 23 hours ago
$190
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sun, May 24 from Denver Intl. to Midway Intl., returning Mon, Jun 1, priced at $190 found 23 hours ago