Deals on vacations and trips to Glenwood

Save when you book Glenwood package deals

Choose two or more items and save on your trip:

Glenwood flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $920, price is now $610 per person
$610
per person
Nov 22 - Nov 25
found 24 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,161, price is now $1,387 per person
$1,387
per person
Nov 24 - Nov 30
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and A 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and coffee shop.
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Save 100% on your flight
Price was $998, price is now $677 per person
$677
per person
Nov 24 - Nov 30
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-out are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,437, price is now $981 per person
$981
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,085, price is now $745 per person
$745
per person
Nov 25 - Nov 29
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Top Glenwood hotels deals

Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Free Cancellation
$118 nightly
The price is $139 total per night
$139 total
Oct 4 - Oct 5
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and a free airport shuttle. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Free Cancellation
$162 nightly
The price is $188 total per night
$188 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Free WiFi
Restaurant
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
$169 nightly
The price is $199 total per night
$199 total
Sep 20 - Sep 21
Total with taxes and fees
Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Luggage storage is also provided.
Pet friendly
Parking included
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave Bridgeview IL
Free Cancellation
Reserve now, pay when you stay
$53 nightly
The price is $59 total per night
$59 total
Oct 5 - Oct 6
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4.5 out of 5
17300 S Halsted St Hazel Crest IL
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $183 total per night
$183 total
Oct 14 - Oct 15
Total with taxes and fees
This luxury resort features a casino, a full-service spa, and 8 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 4 bars/lounges and enjoy perks like free self parking.
Hot Tub
Spa
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd. East Chicago IN
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $174 total per night
$174 total
Oct 5 - Oct 6
Total with taxes and fees
A casino, 5 restaurants, and a 24-hour gym are all featured at this Art Deco hotel. Business travelers can take advantage of the 24-hour business center. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Parking included
Restaurant
Don't see what you're looking for?
See all available properties in Glenwood
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Glenwood?
Travelocity has great package deals to Glenwood, as well as flights and hotels, from an impressive $610. With the money you save, you could throw in some cool tours or possibly even tack on some extra nights to your vacation.
Where can I get the best vacation package deals for Glenwood?
Find your dream escape at Travelocity. With access to 400 air carriers and at least 1,000,000 properties across the globe, selecting the ultimate Glenwood package deal couldn't be simpler.
Why should I book my Glenwood vacation bundle with Travelocity?
You'll not only enjoy huge savings, but you'll also have access to our round-the-clock support, quality service and a Price Match Guarantee. Wander across the globe, discover lesser-known sights and make unforgettable memories — we'll take care of the little details.
Can I save money on my Glenwood car rental if I bundle it with a hotel or flight?
Most definitely — and booking one of our Glenwood vacation packages is the simplest way to do this. Bundle any combination of a hotel, flight, car and tour and score awesome discounts. The more you bundle, the more you'll save. There are so many big-name sights around Glenwood to put on your bucket list, including Six Flags Great America (60 mi from Glenwood). Nothing beats exploring places like this with the freedom of your own wheels.

Photos of local treasures

Browse Glenwood vacation photos for more inspiration