Search Deals onGlenwood Vacation Packages
Glenwood Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Save 100% on your flight
Price was $998, price is now $710 per person
$710
per person
Nov 11 - Nov 15
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.
Level Chicago Fulton Market
Save 100% on your flight
Price was $2,281, price is now $1,424 per person
$1,424
per person
Oct 5 - Oct 9
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.
Great! But parking was bad.
Reviewed on Aug 26, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,706, price is now $1,144 per person
$1,144
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
隔音效果差
Reviewed on Aug 27, 2026
The Langham, Chicago
Save 100% on your flight
Price was $1,800, price is now $1,268 per person
$1,268
per person
Nov 20 - Nov 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 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
Price was $1,226, price is now $870 per person
$870
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.
Reviewed on Aug 29, 2026
Hotel Riu Plaza Chicago
Price was $1,227, price is now $880 per person
$880
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
Could have had better music @ the rooftop lounge it was kind of boring. No ice machine for the guest I had to get ice from the bar in the lobby. The bar maid because angry when I ask for less ice her response was ( Oh My God ) and refuse to take back the giant bag of ice that she was giving me. I had to go behind the bar and dump some of it out myself. Lol
Except for that incident the hotel was great.
Reviewed on Aug 29, 2026
The Belfry House
Save 100% on your flight
Price was $1,091, price is now $788 per person
$788
per person
Oct 15 - Oct 19
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Williams Bay. Enjoy free WiFi, free parking, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. Popular attractions Geneva Lake and Kishwauketoe Nature Conservancy are located nearby.
Perfect stay for our anniversary trip!
Reviewed on Aug 28, 2026
Level Chicago - River North
Price was $1,343, price is now $975 per person
$975
per person
Oct 15 - Oct 18
found 18 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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.
Very nice hotel, the view was nice the room was clean and staff was very helpful definitely recommend!
Reviewed on Aug 29, 2026
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.
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$107 Roundtrip, found 2 hours ago
$107
Roundtrip
found 2 hours ago
Mon, Sep 21 - Tue, Sep 22
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Thu, Sep 24 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Sat, Oct 10 - Tue, Oct 13
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$236 Roundtrip, found 1 hour ago
$236
Roundtrip
found 1 hour ago
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