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Glenwood

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Glenwood Flights as Low as $138

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

Frontier Airlines
Wed, Sep 30 - Sat, Oct 3
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138 Roundtrip, found 9 hours ago
$138
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Oct 3, priced at $138 found 9 hours ago
Frontier Airlines
Sat, Sep 12 - Sun, Sep 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Sun, Sep 13, priced at $189 found 2 days ago
Delta
Wed, Sep 30 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$192 Roundtrip, found 9 hours ago
$192
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $192 found 9 hours ago
Frontier Airlines
Tue, Sep 1 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$210 Roundtrip, found 5 hours ago
$210
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Sep 8, priced at $210 found 5 hours ago
Frontier Airlines
Tue, Sep 22 - Wed, Oct 7
MCO
Orlando Intl.
MDW
Midway Intl.
$210 Roundtrip, found 11 hours ago
$210
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Orlando Intl. to Midway Intl., returning Wed, Oct 7, priced at $210 found 11 hours ago
Frontier Airlines
Tue, Aug 18 - Tue, Aug 25
DEN
Denver Intl.
MDW
Midway Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Denver Intl. to Midway Intl., returning Tue, Aug 25, priced at $220 found 1 day ago
Frontier Airlines
Tue, Jul 21 - Tue, Jul 28
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$236 Roundtrip, found 23 hours ago
$236
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Louis Armstrong New Orleans Intl. to Midway Intl., returning Tue, Jul 28, priced at $236 found 23 hours ago
Frontier Airlines
Tue, Jul 14 - Thu, Jul 30
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$255 Roundtrip, found 11 hours ago
$255
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Charlotte-Douglas Intl. to Midway Intl., returning Thu, Jul 30, priced at $255 found 11 hours ago
Delta
Wed, Sep 2 - Wed, Sep 9
RIC
Richmond Intl.
MDW
Midway Intl.
$257 Roundtrip, found 11 hours ago
$257
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Sep 2 from Richmond Intl. to Midway Intl., returning Wed, Sep 9, priced at $257 found 11 hours ago
Frontier Airlines
Tue, Aug 11 - Tue, Aug 18
LGA
LaGuardia
MDW
Midway Intl.
$258 Roundtrip, found 11 hours ago
$258
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from LaGuardia to Midway Intl., returning Tue, Aug 18, priced at $258 found 11 hours ago
Delta
Tue, Aug 18 - Fri, Aug 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$280 Roundtrip, found 3 days ago
$280
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Fri, Aug 28, priced at $280 found 3 days ago
Delta
Sat, Jul 18 - Tue, Jul 28
GSP
Greenville-Spartanburg Intl.
MDW
Midway Intl.
$289 Roundtrip, found 11 hours ago
$289
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Jul 18 from Greenville-Spartanburg Intl. to Midway Intl., returning Tue, Jul 28, priced at $289 found 11 hours ago
Delta
Tue, Oct 13 - Sat, Oct 17
DAL
Love Field
MDW
Midway Intl.
$311 Roundtrip, found 4 hours ago
$311
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Oct 13 from Love Field to Midway Intl., returning Sat, Oct 17, priced at $311 found 4 hours ago
Delta
Sat, Jul 4 - Sat, Jul 4
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$330 Roundtrip, found 1 day ago
$330
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 4 from John F. Kennedy Intl. to Midway Intl., returning Sat, Jul 4, priced at $330 found 1 day ago
Delta
Tue, Jun 30 - Mon, Jul 6
MCI
Kansas City Intl.
MDW
Midway Intl.
$331 Roundtrip, found 9 hours ago
$331
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 30 from Kansas City Intl. to Midway Intl., returning Mon, Jul 6, priced at $331 found 9 hours ago
Delta
Tue, Jun 23 - Fri, Jul 3
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$394 Roundtrip, found 5 days ago
$394
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 23 from Southwest Florida Intl. to Midway Intl., returning Fri, Jul 3, priced at $394 found 5 days 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 September, 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 $138, 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 $138 right now, why wait?

Glenwood Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$138

Last Minute Hotel Deals in Glenwood

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! (1,034 reviews)
"Property was ok… washer was broken they didn’t care nor compensated me for it the pool area was horrible had it covered"

Reviewed on Jun 14, 2026

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Holiday Inn Chicago – Midway Airport S by IHG
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! (1,927 reviews)
"Cliffnotes version; Thursday June 11th (tornado warnings) Couldn't get into room until after 8pm (check in 3pm) Desk staff horrendous, on her personal phone while telling me 'there are no rooms available' (due to they're not ready...left that part out) Room was musty (AC was off on a 94degree day, ..."

Reviewed on Jun 14, 2026

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Sleep Inn Midway Airport Bedford Park
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! (1,090 reviews)
"We experienced a power outage for our stay. The staff assisted us to our room. However, the power did not ever resume, it was difficult to pack to leave. Our stay was fine considering the limitations."

Reviewed on Jun 12, 2026

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DoubleTree by Hilton Chicago - Alsip
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! (1,348 reviews)
"Clean and maintained property. It looks like the rooms have been remolded recently. I stay in “hotel block” off Cicero often. I will say this location was very close to the street which is a little more noisy than other hotels."

Reviewed on Jun 14, 2026

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

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located ...
7.4/10 Good! (352 reviews)
"I loved it"

Reviewed on Jun 11, 2026

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Motel 6 - Chicago, IL
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! (433 reviews)
"The hotel was clean and the staff were amazing and very helpful. However, I did not feel safe during my stay, and in my opinion, it is not the right hotel for families."

Reviewed on Jun 14, 2026

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Wind Creek Southland Casino and Hotel
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! (1,482 reviews)
"Smelled terrible, shower didn’t work, Roaches etc. I was actually scared to get in the bed. Stayed here last minute on a flight cancellation. NEVER AGAIN"

Reviewed on Jun 12, 2026

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Motel 6 Bridgeview, IL
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 (1,017 reviews)
"It's a ok place to stay for the price. Everything is remodeled, so it's clean in the rooms. The pool is still needing remodeling, and it's no restaurant on the property, but it's a clean place to stay"

Reviewed on Jun 14, 2026

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Chicago Lake Shore Hotel
See all 940 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.