Search Deals onGlenwood Vacation Packages
Glenwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $615, price is now $406 per person
$406
per person
Nov 6 - Nov 9
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.
No proper Bar area and breakfast
Small front lobby
Reviewed on Sep 30, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,500, price is now $856 per person
$856
per person
Nov 4 - Nov 7
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.
Swissotel - Chicago
Save 100% on your flight
Price was $1,099, price is now $673 per person
$673
per person
Dec 11 - Dec 17
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.
The room was cold, and I wasn't able to turn the heat on.
Reviewed on Sep 30, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,203, price is now $739 per person
$739
per person
Nov 6 - Nov 9
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
Save 100% on your flight
Price was $1,006, price is now $646 per person
$646
per person
Nov 6 - Nov 9
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.
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $960, price is now $628 per person
$628
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). 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
Save 100% on your flight
Price was $848, price is now $556 per person
$556
per person
Dec 2 - Dec 6
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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Chicago Marriott Southwest at Burr Ridge
Save 100% on your flight
Price was $616, price is now $408 per person
$408
per person
Nov 12 - Nov 16
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Burr Ridge. Enjoy a 24-hour fitness center, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Burr Ridge Village Center and Flagg Creek Golf Course are located nearby.
Glenwood Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Glenwood Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Oct 29 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$116 Roundtrip, found 4 hours ago
$116
Roundtrip
found 4 hours ago
Sat, Dec 5 - Sat, Dec 12
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 21 hours ago
$117
Roundtrip
found 21 hours ago
Sat, Nov 7 - Tue, Nov 17
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$167 Roundtrip, found 19 hours ago
$167
Roundtrip
found 19 hours ago
Tue, Nov 10 - Thu, Nov 19
IAH
George Bush Intercontinental
MDW
Midway Intl.
$196 Roundtrip, found 11 hours ago
$196
Roundtrip
found 11 hours ago
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