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Cheap flights from Albany, New York to Chicago from $101

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Albany, New York to Chicago departing on 2/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Albany, New York to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:35 pm - 7:00 pm
ALB
-
MDW
4h 25m1 stop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$256Southwest
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
5:30 am - 6:55 am
ALB
-
MDW
2h 25mnonstop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$258Southwest
Tue, Jan 20 - Tue, Jan 20
Southwest Logo
5:30 am - 6:55 am
ALB
-
MDW
2h 25mnonstop
Southwest Logo
2:20 pm - 10:05 pm
MDW
-
ALB
6h 45m2 stops
$261Southwest
Tue, Jan 20 - Tue, Jan 20
Southwest Logo
5:50 am - 7:25 am
ALB
-
MDW
2h 35mnonstop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$281Southwest
Sat, Jan 24 - Mon, Jan 26
Delta Logo
2:30 pm - 10:07 pm
ALB
-
MDW
8h 37m1 stop
Delta Logo
9:32 am - 4:28 pm
MDW
-
ALB
5h 56m1 stop
$291Delta
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
6:00 am - 11:35 am
ALB
-
MDW
6h 35m1 stop
Southwest Logo
2:20 pm - 10:05 pm
MDW
-
ALB
6h 45m2 stops
$294Southwest
Tue, Jan 20 - Tue, Jan 20
Southwest Logo
5:50 am - 7:25 am
ALB
-
MDW
2h 35mnonstop
Southwest Logo
8:10 am - 6:25 pm
MDW
-
ALB
9h 15m2 stops
$296Southwest
Sat, Jan 24 - Mon, Jan 26
Southwest Logo
1:00 pm - 6:50 pm
ALB
-
MDW
6h 50m2 stops
Southwest Logo
6:50 am - 12:20 pm
MDW
-
ALB
4h 30m1 stop
$306Southwest
Mon, Feb 2 - Wed, Feb 4
Southwest Logo
5:30 am - 6:55 am
ALB
-
MDW
2h 25mnonstop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$311Southwest
Fri, Jan 30 - Mon, Feb 2
Southwest Logo
11:25 am - 7:00 pm
ALB
-
MDW
8h 35m2 stops
Southwest Logo
6:50 am - 12:20 pm
MDW
-
ALB
4h 30m1 stop
$318Southwest
Sat, Jan 24 - Mon, Jan 26

Southwest flights from Albany, New York to Chicago Midway Airport

Our best Southwest deals on Albany, New York to Chicago Midway Airport flight tickets
Southwest
Jan 17
ALB3:35 pmAlbany Intl
4h 25m
1 stop
MDW7:00 pmChicago Midway
Jan 18
MDW1:25 pmChicago Midway
1h 50m
ALB4:15 pmAlbany Intl
$256
Find similar
Southwest
Jan 20
ALB5:30 amAlbany Intl
2h 25m
MDW6:55 amChicago Midway
Jan 20
MDW1:25 pmChicago Midway
1h 50m
ALB4:15 pmAlbany Intl
$258
Find similar
Southwest
Jan 20
ALB5:30 amAlbany Intl
2h 25m
MDW6:55 amChicago Midway
Jan 20
MDW2:20 pmChicago Midway
6h 45m
2 stops
ALB10:05 pmAlbany Intl
$261
Find similar

Delta flights from Albany, New York to Chicago Midway Airport

Our best Delta deals on Albany, New York to Chicago Midway Airport flight tickets
Delta
Jan 17
ALB5:30 amAlbany Intl
4h 22m
1 stop
MDW8:52 amChicago Midway
Jan 18
MDW6:14 pmChicago Midway
4h 12m
1 stop
ALB11:26 pmAlbany Intl
$291
Find similar
Delta
Feb 17
ALB5:50 pmAlbany Intl
5h 54m
1 stop
MDW10:44 pmChicago Midway
Feb 20
MDW6:17 pmChicago Midway
4h 07m
1 stop
ALB11:24 pmAlbany Intl
$319
Find similar
Delta
Mar 11
ALB6:00 amAlbany Intl
3h 46m
1 stop
MDW8:46 amChicago Midway
Mar 18
MDW9:32 amChicago Midway
5h 51m
1 stop
ALB4:23 pmAlbany Intl
$321
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Albany, New York to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Albany, New York to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/17

3:35 pm-7:00 pm

1 stop4h 25m

Chicago Midway

Sun 1/18

1:25 pm-4:15 pm

Nonstop1h 50m

$256

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 1/20

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Tue 1/20

1:25 pm-4:15 pm

Nonstop1h 50m

$258

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 1/20

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Tue 1/20

2:20 pm-10:05 pm

2 stops6h 45m

$261

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/24

5:50 am-7:25 am

Nonstop2h 35m

Chicago Midway

Mon 1/26

1:25 pm-4:15 pm

Nonstop1h 50m

$281

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/17

2:30 pm-10:07 pm

1 stop8h 37m

Chicago Midway

Sun 1/18

9:32 am-4:28 pm

1 stop5h 56m

$291

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 1/20

6:00 am-11:35 am

1 stop6h 35m

Chicago Midway

Tue 1/20

2:20 pm-10:05 pm

2 stops6h 45m

$294

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/24

5:50 am-7:25 am

Nonstop2h 35m

Chicago Midway

Mon 1/26

8:10 am-6:25 pm

2 stops9h 15m

$296

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 2/2

1:00 pm-6:50 pm

2 stops6h 50m

Chicago Midway

Wed 2/4

6:50 am-12:20 pm

1 stop4h 30m

$306

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Fri 1/30

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Mon 2/2

1:25 pm-4:15 pm

Nonstop1h 50m

$311

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/24

11:25 am-7:00 pm

2 stops8h 35m

Chicago Midway

Mon 1/26

6:50 am-12:20 pm

1 stop4h 30m

$318

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Albany, New York to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Albany, New York, with most prices found around $234. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Albany, New York during the month February is also very affordable. Most momondo users find prices during this month for around $299.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Albany, New York. The lowest ticket price found for a Tuesday departure recently was $402. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Albany, New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $508.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Albany, New York in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $418 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $467. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Albany Intl to Chicago Midway flight route?

Fly from Albany Intl to Chicago Midway for the best Albany Intl - Chicago Midway flight prices

What cabin class options are available on Albany Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on Albany Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Albany, New York to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Albany, New York to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Albany, New York to Chicago Midway Airport (ALB to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Albany, New York to Chicago Midway Airport

Best Price Found

$252

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Albany, New York in the past 72 hours is $252. The best round-trip flight deal from Albany, New York to Chicago Midway Airport found on momondo in the last 72 hours is $417.
The fastest flight from Albany, New York to Chicago Midway Airport takes 2h 10m
Direct flights go from Albany, New York to Chicago Midway Airport every day.
Search flight deals

  • How far is Albany Intl to Chicago Midway by plane?

    The straight-line distance from Albany Intl to Chicago Midway is 717.3 mi. In terms of flight time, this usually takes a little over 2h 10m.

  • When did momondo last update prices for flights from Albany Intl Airport to Chicago Midway Airport?

    Prices for flights from Albany Intl Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Albany Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Albany Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Albany Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Albany, New York to Chicago Midway Airport?

  • What is the most popular airline from Albany, New York to Chicago Midway Airport?

Best airlines flying from Albany, New York to Chicago Midway Airport

Compare and see reviews for airlines that fly from Albany, New York to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $134Free CancellationRating
7.9
8,005 reviews
Search Delta flights
SouthwestPriceFrom $229Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

  • Southwest Flights From Albany, New York to Chicago Midway Airport

    Southwest flight deals from Albany, New York to Chicago Midway Airport start from $229 round-trip. Over the 4 Southwest flights for this route in a normal week, average airfare is usually $353 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Albany to Chicago?

It is quick and easy to find Albany to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Albany to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Albany to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Albany to Chicago?

Once you have performed a search for Albany to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Albany to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Albany to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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