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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
Delta
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Delta
Frontier Airlines
Frontier Airlines
Delta
Frontier Airlines
Delta
Frontier Airlines
Frontier Airlines
Frontier Airlines
Delta
Delta
Delta
Delta

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

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

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

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

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

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

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

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

Hilton Chicago/Oak Lawn
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.