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Midway

$111+ Cheap flights from Albany, NY (ALB) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
ALB — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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Cheap flight deals from Albany to Midway

Cheapest flights from Albany to Midway
Explore the most affordable flight options available from Albany to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.

This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:30 pm
ALB
-
MDW
1 stop8h 40m
Southwest
Tue 6/97:45 am
MDW
-
ALB
Nonstop2h 00m
Southwest
Deal found 4/23$295
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:35 am
ALB
-
MDW
2 stops7h 50m
Southwest
Tue 9/812:45 pm
MDW
-
ALB
Nonstop1h 50m
Southwest
Deal found 4/25$300
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:50 am
ALB
-
MDW
Nonstop2h 15m
Southwest
Mon 6/16:50 pm
MDW
-
ALB
Nonstop1h 55m
Southwest
Deal found 4/27$302
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:05 pm
ALB
-
MDW
1 stop6h 15m
Southwest
Mon 9/141:30 pm
MDW
-
ALB
Nonstop1h 55m
Southwest
Deal found 4/23$303
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ALB
-
MDW
1 stop3h 43m
Delta
Tue 6/99:17 am
MDW
-
ALB
1 stop6h 05m
Delta
Deal found 4/27$305
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:00 am
ALB
-
MDW
1 stop3h 43m
Delta
Tue 5/269:22 am
MDW
-
ALB
1 stop5h 45m
Delta
Deal found 4/24$315
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:25 pm
ALB
-
MDW
Nonstop2h 10m
Southwest
Mon 6/16:50 pm
MDW
-
ALB
Nonstop1h 55m
Southwest
Deal found 4/27$319

Find flight deals from Albany to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Albany (ALB) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(Southwest)

One-way from

$111
(Southwest)

Popular in

April

Cheapest in

October

Average price

$504

Good round-trip deal

$457 or less

Good one-way deal

$217 or less
Provider with most accurate pricing for Albany Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Albany Intl-Chicago Midway flights.
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From Albany Intl to Chicago Midway
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One-way flight from Albany Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 2026
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Price to beat on a round-trip flight from Albany Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Albany Intl to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Albany to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
Use the filters below to find and compare flights from Albany to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Fri 6/5

4:30 pm-12:10 am

1 stop8h 40m

Chicago Midway

Tue 6/9

7:45 am-10:45 am

Nonstop2h 00m

$295

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 9/2

8:35 am-3:25 pm

2 stops7h 50m

Chicago Midway

Tue 9/8

12:45 pm-3:35 pm

Nonstop1h 50m

$300
Quickest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 6/4

3:20 pm-4:35 pm

Nonstop2h 15m

Chicago Midway

Mon 6/8

6:50 pm-9:45 pm

Nonstop1h 55m

$319

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 7/8

6:55 pm-8:15 pm

Nonstop2h 20m

Chicago Midway

Sat 7/11

5:45 pm-8:40 pm

Nonstop1h 55m

$333

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 8/10

5:05 pm-10:20 pm

1 stop6h 15m

Chicago Midway

Tue 8/11

8:30 am-11:35 am

Nonstop2h 05m

$347

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 6/1

2:55 pm-8:35 pm

2 stops6h 40m

Chicago Midway

Wed 6/3

7:40 am-4:00 pm

2 stops7h 20m

$349

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 6/6

6:10 pm-7:30 pm

Nonstop2h 20m

Chicago Midway

Wed 6/10

6:15 pm-9:10 pm

Nonstop1h 55m

$357

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 8/27

10:15 am-4:15 pm

1 stop7h 00m

Chicago Midway

Sun 8/30

6:15 pm-9:15 pm

Nonstop2h 00m

$359

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sun 7/19

6:05 am-9:08 am

1 stop4h 03m

Chicago Midway

Tue 7/21

9:19 am-4:25 pm

1 stop6h 06m

$369

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 7/23

6:00 am-9:08 am

1 stop4h 08m

Chicago Midway

Mon 7/27

9:20 am-4:25 pm

1 stop6h 05m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 20 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Albany, New York-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Albany, New York-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Albany, New York-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Albany, New York-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Albany, New York-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Albany to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Albany with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Albany to Chicago Midway Airport

What is the cheapest time of day to fly from ALB to MDW?

Find hourly flight availability from Albany to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 28, 2026.

It’s typically best to fly out from Albany, New York to Chicago Midway Airport in the afternoon. Doing so could potentially save you 15% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost to fly round-trip from Albany, New York to Chicago Midway Airport?

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated April 28, 2026.
Peruse reviews from past customers who have flown with Southwest from Albany to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Albany to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Albany to Chicago Midway?

    For a flight from Albany to Chicago Midway, you will be flying from Albany Intl. Albany Intl (ALB) is just 7.4 mi from the center of the city. Albany Intl is the only Albany airport and it handles 1 outbound flight to Chicago Midway per day. 1 airline has flights to Chicago Midway from Albany Intl on a regular basis.

  • How long is the flight from Albany, New York to Chicago Midway Airport?

    There are many flights that can get you from Albany, New York to Chicago Midway Airport in 8h 40m. Fly via Southwest to get the fastest option. Airlines will cover a distance of 715 mi.

  • What is the cheapest airline to fly from Albany, New York to Chicago Midway Airport round-trip?

    Our cheapest airline available from Albany, New York to Chicago Midway Airport is Southwest. Our recent data shows that you can find tickets from as low as $266 on this airline. This flight start at 27% lower than the current average price 3 months from now.

  • What are the cheapest flights from Albany, New York to Chicago Midway Airport?

    On average you can expect to pay $409 for a flight from Albany, New York to Chicago Midway Airport. The cheapest flight overall is $142 while the most popular route, (Albany Intl - Chicago Midway) is currently priced at $285.

  • Can I find deals for flights from Albany to Midway that include hotel bookings?

    Yes. In addition to deals on Albany to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Albany to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Albany to Midway.

  • Can I find deals for business class flights from Albany to Midway?

    Yes. Cheapflights offers flight deals from Albany to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Albany to Midway

Discover the top airline that operate flights from Albany to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$266Average$364FlexibilityNo cancel feeOn-time63%

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