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.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
Save 100% on your flight
Price was $575, price is now $348 per person
$348
per person
Jan 26 - Feb 2
found 12 hours 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 free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,198, price is now $661 per person
$661
per person
Feb 14 - Feb 22
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $820, price is now $494 per person
$494
per person
Mar 13 - Mar 16
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $820, price is now $504 per person
$504
per person
Mar 13 - Mar 16
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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $827, price is now $520 per person
$520
per person
Mar 13 - Mar 16
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $640, price is now $405 per person
$405
per person
Feb 20 - Feb 23
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $702, price is now $448 per person
$448
per person
Mar 13 - Mar 16
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.
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
Save 100% on your flight
Price was $585, price is now $377 per person
$377
per person
Feb 14 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Arrowhead Golf Club are located nearby.

Glenwood Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $892, price is now $502 per person
$502
per person
Jan 26 - Feb 2
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,220, price is now $638 per person
$638
per person
Jan 26 - Feb 2
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,135, price is now $631 per person
$631
per person
Mar 7 - Mar 12
found 16 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $927, price is now $528 per person
$528
per person
Mar 7 - Mar 12
found 14 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Thu, Jan 8 - Mon, Jan 19
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$84 Roundtrip, found 4 days ago
$84
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Sky Harbor Intl. to Midway Intl., returning Mon, Jan 19, priced at $84 found 4 days ago
Frontier Airlines
Wed, Dec 31 - Wed, Jan 7
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$109 Roundtrip, found 17 hours ago
$109
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Dec 31 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jan 7, priced at $109 found 17 hours ago
Frontier Airlines
Fri, Jan 16 - Mon, Jan 19
DEN
Denver Intl.
MDW
Midway Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Denver Intl. to Midway Intl., returning Mon, Jan 19, priced at $120 found 1 day ago
Frontier Airlines
Wed, Dec 31 - Fri, Jan 2
IAH
George Bush Intercontinental
MDW
Midway Intl.
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Dec 31 from George Bush Intercontinental to Midway Intl., returning Fri, Jan 2, priced at $152 found 4 days ago