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Glenwood

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Glenwood Flights as Low as $66

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

Frontier Airlines
Tue, Jun 9 - Wed, Jun 17
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$66 Roundtrip, found 2 hours ago
$66
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jun 17, priced at $66 found 2 hours ago
Delta
Wed, Jul 1 - Wed, Jul 22
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 2 hours ago
$117
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Jul 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Jul 22, priced at $117 found 2 hours ago
Delta
Tue, Jun 16 - Wed, Jul 1
IAH
George Bush Intercontinental
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 16 from George Bush Intercontinental to Midway Intl., returning Wed, Jul 1, priced at $197 found 1 day ago
Delta
Tue, Jun 9 - Wed, Jun 17
MCO
Orlando Intl.
MDW
Midway Intl.
$201 Roundtrip, found 8 hours ago
$201
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Jun 9 from Orlando Intl. to Midway Intl., returning Wed, Jun 17, priced at $201 found 8 hours ago
Frontier Airlines
Tue, Jun 30 - Tue, Jul 7
DEN
Denver Intl.
MDW
Midway Intl.
$205 Roundtrip, found 9 hours ago
$205
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Jun 30 from Denver Intl. to Midway Intl., returning Tue, Jul 7, priced at $205 found 9 hours ago
Frontier Airlines
Wed, Jul 1 - Tue, Jul 21
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$205 Roundtrip, found 17 hours ago
$205
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Jul 1 from Raleigh - Durham Intl. to Midway Intl., returning Tue, Jul 21, priced at $205 found 17 hours ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 16 hours ago
$219
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $219 found 16 hours ago
Frontier Airlines
Mon, Aug 10 - Wed, Aug 19
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Sky Harbor Intl. to Midway Intl., returning Wed, Aug 19, priced at $224 found 1 day ago
Delta
Wed, Jun 17 - Fri, Jun 26
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 17 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Fri, Jun 26, priced at $235 found 3 days ago
Frontier Airlines
Thu, May 21 - Wed, May 27
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$246 Roundtrip, found 5 days ago
$246
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, May 21 from Washington Dulles Intl. to Midway Intl., returning Wed, May 27, priced at $246 found 5 days ago
Frontier Airlines
Tue, Jul 28 - Mon, Aug 3
BUF
Buffalo Niagara Intl.
MDW
Midway Intl.
$250 Roundtrip, found 3 days ago
$250
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jul 28 from Buffalo Niagara Intl. to Midway Intl., returning Mon, Aug 3, priced at $250 found 3 days ago
Frontier Airlines
Mon, Jul 27 - Sat, Aug 15
LAS
Harry Reid Intl.
MDW
Midway Intl.
$254 Roundtrip, found 17 hours ago
$254
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Mon, Jul 27 from Harry Reid Intl. to Midway Intl., returning Sat, Aug 15, priced at $254 found 17 hours ago
Delta
Sat, Jul 25 - Sat, Aug 8
DAL
Love Field
MDW
Midway Intl.
$311 Roundtrip, found 5 days ago
$311
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 25 from Love Field to Midway Intl., returning Sat, Aug 8, priced at $311 found 5 days ago
Delta
Tue, May 26 - Tue, Jun 2
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$353 Roundtrip, found 6 days ago
$353
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, May 26 from Ronald Reagan Washington National to Midway Intl., returning Tue, Jun 2, priced at $353 found 6 days ago
Delta
Wed, May 20 - Tue, May 26
ILM
Wilmington Intl.
MDW
Midway Intl.
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 20 from Wilmington Intl. to Midway Intl., returning Tue, May 26, priced at $364 found 1 day ago
Delta
Sun, May 24 - Wed, May 27
ORF
Norfolk Intl.
MDW
Midway Intl.
$394 Roundtrip, found 12 hours ago
$394
Roundtrip
found 12 hours ago
Select Delta flight, departing Sun, May 24 from Norfolk Intl. to Midway Intl., returning Wed, May 27, priced at $394 found 12 hours ago

Cheap Flights to Glenwood

Fall in love at first flight with your vacation to Glenwood by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Glenwood on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Glenwood, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Glenwood

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Glenwood with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the MDW airport.

What is the cheapest month to fly to Glenwood?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Glenwood are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Glenwood?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Glenwood.

What airport is best to fly into Glenwood?

When you’re planning your trip to Glenwood, convenience is the name of the game. Luckily, Glenwood Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Glenwood must-do list.

How much are flights to Glenwood?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Glenwood on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $66, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Glenwood?

The trick to saving a stack of cash on your flight to Glenwood? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $66 right now, why wait?

Glenwood Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$66

Last Minute Hotel Deals in Glenwood

Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8/10 Very Good! (1,866 reviews)
Breakfast was good.

Reviewed on May 11, 2026

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Sleep Inn Midway Airport Bedford Park
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
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,000 reviews)
It was in a good location right next to a bus stop but it looked like they were fixing the place up and I’m sure it will be great when it’s done but it’s not there yet

Reviewed on May 9, 2026

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Holiday Inn Chicago – Midway Airport S by IHG
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,045 reviews)
Clean room with comfortable bed. No complimentary breakfast. No microwave in room. Pool closed. Parking was good. If there was a fitness room I couldn’t find it. Outside visiting area very convenient.

Reviewed on May 11, 2026

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DoubleTree by Hilton Chicago - Alsip
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
6.8/10 (1,008 reviews)
This is an older 2 story property with great big refinished rooms with lake views. Daily attention to room turndown excellent! Front desk staff very nice. Location is wonderful with the highway close, biking path and water close, food a short walk, and museums a short drive. Parking is free. Downside ...

Reviewed on May 11, 2026

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Chicago Lake Shore Hotel
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe ...
9.2/10 Wonderful! (373 reviews)
I don't like the fact that you allow kids at this property. They run around unsupervised, going to the pool. The property should be for people 21 and older!!

Reviewed on May 12, 2026

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Wind Creek Southland Casino and Hotel
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

2.5 out of 5
6500 S Cicero Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,317 reviews)
Excellent place to stay at perfect location and breakfast was also amazing

Reviewed on May 12, 2026

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Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
9625 S 76th Ave Bridgeview IL
Stay at this motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,465 reviews)
Great rooms good customer service

Reviewed on May 11, 2026

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Motel 6 Bridgeview, IL
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave Oak Lawn IL
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,332 reviews)
family stayed at the Hilton Chicago/Oak Lawn for four nights, and overall the experience was disappointing. The bathroom door made loud noises every time it opened, and housekeeping failed to clean our room even after I personally requested full service and towels at the front desk before leaving ...

Reviewed on May 12, 2026

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Hilton Chicago/Oak Lawn
See all 946 properties in Glenwood
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.