$57 Cheap Flights from Albany (ALB) to Chicago (MDW)

View $57 flight on Sat, Aug 30, 2025Opens in a new window

Popular airlines from Albany Intl. Airport (ALB) to Chicago Midway Airport (MDW)

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Cheap Flights from Albany to Chicago (ALB-MDW)

Prices were available within the past 7 days and start at $57 for one-way flights and $131 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Sep 8 - Wed, Sep 10
ALB
Albany
MDW
Chicago
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Sep 8 from Albany to Chicago, returning Wed, Sep 10, priced at $131 found 1 day ago
Southwest Airlines
Tue, Oct 21 - Sat, Oct 25
ALB
Albany
MDW
Chicago
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Albany to Chicago, returning Sat, Oct 25, priced at $133 found 1 day ago
Southwest Airlines
Tue, Oct 21 - Sat, Oct 25
ALB
Albany
MDW
Chicago
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Albany to Chicago, returning Sat, Oct 25, priced at $138 found 1 day ago
Southwest Airlines
Tue, Sep 9 - Fri, Sep 12
ALB
Albany
MDW
Chicago
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Albany to Chicago, returning Fri, Sep 12, priced at $140 found 1 day ago
Southwest Airlines
Tue, Oct 21 - Sat, Oct 25
ALB
Albany
MDW
Chicago
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Albany to Chicago, returning Sat, Oct 25, priced at $140 found 1 day ago
Southwest Airlines
Sat, Sep 20 - Wed, Sep 24
ALB
Albany
MDW
Chicago
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Albany to Chicago, returning Wed, Sep 24, priced at $143 found 1 day ago
Southwest Airlines
Tue, Sep 9 - Fri, Sep 12
ALB
Albany
MDW
Chicago
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Albany to Chicago, returning Fri, Sep 12, priced at $145 found 1 day ago
Southwest Airlines
Mon, Sep 1 - Wed, Sep 3
ALB
Albany
MDW
Chicago
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Sep 1 from Albany to Chicago, returning Wed, Sep 3, priced at $146 found 1 day ago
Southwest Airlines
Fri, Oct 31 - Sun, Nov 2
ALB
Albany
MDW
Chicago
$147 Roundtrip, found 17 hours ago
$147
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Albany to Chicago, returning Sun, Nov 2, priced at $147 found 17 hours ago
Delta
Sat, Aug 30 - Mon, Sep 1
ALB
Albany
MDW
Chicago
$208 Roundtrip, found 13 hours ago
$208
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Aug 30 from Albany to Chicago, returning Mon, Sep 1, priced at $208 found 13 hours ago

Find the cheapest month to fly from Albany (ALB) to Chicago (MDW)

September is typically the cheapest month to fly

From $176 - $610 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $376
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $376
Flights from Albany (ALB) to Chicago (MDW)
Origin airport
Albany Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$113
Distance
714 mi
Average flight time
1 hour 12 mins

Albany to Chicago Flights

The cheapest times to fly from Albany to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Albany to Chicago are during the month of September. You can find some of the cheapest flights from Albany to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Albany to Chicago

Sunday is one of the best days to book for cheap flights from Albany to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Albany to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Albany to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $57 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Albany to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Albany to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW) cost?
Cheap round-trip fares from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW) start at $140. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving ALB on August 1 2025 and touching down at MDW. The price was last updated on July 10 2025 and has not changed since.
What is the cheapest month to fly from ALB to MDW?
The cheapest flights from ALB to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
Fly nonstop from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from ALB to MDW?
With fares starting at $70 for a one-way journey from ALB to MDW, Southwest Airlines is currently the cheapest airline operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ALB on September 6 2025. Prices were last updated on July 10 2025 and have not changed since.
How many flights per day from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
On average, there is just 1 nonstop flight leaving from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW) each day. If this doesn't work with your itinerary, think about flights with a layover. Just customize your search results on Expedia to include one or more stops to find a better alternative.
What are the most popular departure times for flights from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
The 5 AM departures from ALB to MDW are the top choice for many travelers. Prices can be higher for these popular slots. If you want to save on your trip, book during off-peak hours.
What day of the week has the most flights from ALB to MDW?
Friday offers the most flights from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW). Consider taking off on this day and you'll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
Take the earliest flight at around 5:45AM UTC-5, heading out of Albany Intl. Airport (ALB). You'll be in the air for around 2h 30m, touching down at Midway Intl. Airport (MDW) at approximately 7:15AM UTC-6.
How long does it take to fly from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
Flights from ALB to MDW have an average travel time of 2 hours and 30 minutes. The distance between the two airports is 720 mi.
What is the best time to fly from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW) route, travel before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Albany Intl. Airport (ALB)?
Hop on a direct flight from Albany Intl. Airport (ALB) to Chicago and land at O'Hare Intl. Airport (ORD). Another convenient entry point into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from ALB to MDW right before your trip is usually more expensive. But if there's some wiggle room with your departure times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book an ALB to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an ALB to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place will take the hassle out of planning your trip. Simply pick your flights and select from our extensive range of hotels, then customize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Albany Intl. Airport (ALB) to Midway Intl. Airport (MDW)?
It's usually possible to cancel or reschedule your ALB to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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