Search Cheap Flights to
Glenwood

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Glenwood Flights as Low as $131

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

Frontier Airlines
Sat, Jul 18 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 21, priced at $131 found 3 days ago
Frontier Airlines
Sat, Jul 18 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 21, priced at $142 found 3 days ago
Frontier Airlines
Sat, Jul 18 - Thu, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Jul 23, priced at $162 found 3 days ago
Frontier Airlines
Mon, Jul 13 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$172 Roundtrip, found 6 days ago
$172
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Jul 13 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 21, priced at $172 found 6 days ago
Frontier Airlines
Wed, Jul 15 - Mon, Jul 20
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jul 15 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Jul 20, priced at $183 found 6 days ago
Frontier Airlines
Tue, Jul 21 - Sat, Jul 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$184 Roundtrip, found 5 days ago
$184
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Jul 25, priced at $184 found 5 days ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 23
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 23, priced at $185 found 5 days ago
Delta
Wed, Sep 16 - Tue, Sep 29
MEM
Memphis Intl.
MDW
Midway Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 16 from Memphis Intl. to Midway Intl., returning Tue, Sep 29, priced at $197 found 4 days ago
Frontier Airlines
Tue, Jul 14 - Wed, Jul 15
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$236 Roundtrip, found 1 day ago
$236
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Detroit Metropolitan Wayne County to Midway Intl., returning Wed, Jul 15, priced at $236 found 1 day ago
Frontier Airlines
Wed, Jul 8 - Wed, Jul 15
MCO
Orlando Intl.
MDW
Midway Intl.
$236 Roundtrip, found 11 hours ago
$236
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Jul 8 from Orlando Intl. to Midway Intl., returning Wed, Jul 15, priced at $236 found 11 hours ago
Delta
Tue, Aug 18 - Tue, Aug 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 25, priced at $269 found 2 days ago
Frontier Airlines
Sun, Jul 5 - Thu, Jul 16
ONT
Ontario Intl. Airport
MDW
Midway Intl.
$326 Roundtrip, found 13 hours ago
$326
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sun, Jul 5 from Ontario Intl. Airport to Midway Intl., returning Thu, Jul 16, priced at $326 found 13 hours ago
Delta
Sun, Aug 16 - Sun, Aug 30
BIL
Logan Intl.
MDW
Midway Intl.
$333 Roundtrip, found 11 hours ago
$333
Roundtrip
found 11 hours ago
Select Delta flight, departing Sun, Aug 16 from Logan Intl. to Midway Intl., returning Sun, Aug 30, priced at $333 found 11 hours ago
Delta
Wed, Jul 1 - Wed, Jul 8
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$350 Roundtrip, just found
$350
Roundtrip
just found
Select Delta flight, departing Wed, Jul 1 from Southwest Florida Intl. to Midway Intl., returning Wed, Jul 8, priced at $350 just found
Delta
Wed, Jul 15 - Wed, Jul 22
OKC
Will Rogers World
MDW
Midway Intl.
$398 Roundtrip, found 23 hours ago
$398
Roundtrip
found 23 hours ago
Select Delta flight, departing Wed, Jul 15 from Will Rogers World to Midway Intl., returning Wed, Jul 22, priced at $398 found 23 hours ago
United
Fri, Jun 26 - Sun, Jul 5
MAF
Midland Intl.
MDW
Midway Intl.
$2,165 Roundtrip, found 1 day ago
$2,165
Roundtrip
found 1 day ago
Select United flight, departing Fri, Jun 26 from Midland Intl. to Midway Intl., returning Sun, Jul 5, priced at $2,165 found 1 day 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 July, 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 $131, 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 $131 right now, why wait?

Glenwood Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$131

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 ...
8.4/10 Very Good! (1,016 reviews)
"Checked in on May 29, lobby was very nice, staff was super friendly and accommodating. Room was very comfortable. I would stay here again!"

Reviewed on Jun 6, 2026

Get rates
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! (1,902 reviews)
"I had to switch rooms. The first room, the towel bar had fallen and the AC would not turn on but the young lady at the front desk helped me and it wasn't an issue (I didn't want to be charged for damages!) I was able to switch to a much better room in less than 5 mins. There are a lot of food choices ..."

Reviewed on Jun 5, 2026

Get rates
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! (1,078 reviews)
"Overall not a bad experience. Just rooms need to be cleaned much better. More attention to detail"

Reviewed on Jun 4, 2026

Get rates
DoubleTree by Hilton Chicago - Alsip
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 ...
9.4/10 Exceptional! (417 reviews)
"There is no easy way to get luggage to your room. Check in is on floor 2. You enter on floor 1. If you dont want to pay for valet, you go to the garage, walk an insane distance, take an elevator to a different floor to check in, then make your way alllllllll the way back to your car and carry everything ..."

Reviewed on Jun 7, 2026

Get rates
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! (1,338 reviews)
"Amenities listed on property are NOT accurate. Had to drag my laundry to another hotel. Staff was friendly, manager Glen was not."

Reviewed on Jun 6, 2026

Get rates
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! (344 reviews)
"Nice"

Reviewed on Jun 5, 2026

Get rates
Motel 6 - Chicago, IL
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! (1,466 reviews)
"That’s better"

Reviewed on Jun 3, 2026

Get rates
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 (1,007 reviews)
"It's more than I expected for what I paid. They haven't renovated the pool yet but the rooms are updated and nice. The staff was very friendly and incredibly helpful. You can cast to the TV's from your phone which was great. I could just use all my regular streaming apps. Close enough to downtown ..."

Reviewed on Jun 6, 2026

Get rates
Chicago Lake Shore Hotel
See all 944 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.