Deals on vacations and trips to Glenwood

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Glenwood flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $454, price is now $336 per person
$336
per person
Jan 21 - Jan 23
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $705, price is now $490 per person
$490
per person
Jan 20 - Jan 23
found 22 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Price was $518, price is now $377 per person
$377
per person
Jan 15 - Jan 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport drop-off service. You'll appreciate the area shuttle, free self parking, and terrace.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $680, price is now $496 per person
$496
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,104, price is now $819 per person
$819
per person
Jan 9 - Jan 13
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Glenwood hotels deals

Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel

4.5 out of 5
17300 S Halsted St Hazel Crest IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $200 total per night
$200 total
Dec 1 - Dec 2
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.
Pool
Hot Tub
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
$62 nightly
The price is $69 total per night
$69 total
Nov 16 - Nov 17
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
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
$108 nightly
The price is $125 total per night
$125 total
Dec 6 - Dec 7
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free train station pick-up is offered as well.
Free airport shuttle
Free WiFi
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and a free airport shuttle. A business center, free WiFi in public areas, and express check-out are also on offer.
Pool
Free airport shuttle
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
$101 nightly
The price is $119 total per night
$119 total
Nov 29 - Nov 30
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
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
12801 South Cicero Alsip IL
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $95 total per night
$95 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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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 $336. 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.

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