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$129+ Cheap flights from Albany, NY (ALB) to Chicago (CHI)

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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
ALB — CHI
Jun 14 — Jun 211
Sun 6/14
Sun 6/21
1 adult, Economy
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Cheapflights Tip: The best prices from Albany Intl to Chicago are usually found in September or January, booked 81 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Albany to Chicago

Cheapest flights from Albany to Chicago
Explore the most affordable flight options available from Albany to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.

This American Airlines deal was found by Cheapflights users on 5/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:36 am
ALB
-
ORD
Nonstop2h 34m
American Airlines
Mon 9/218:20 pm
ORD
-
ALB
Nonstop2h 16m
American Airlines
Deal found 5/11$312
This American Airlines deal was found by Cheapflights users on 5/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:26 pm
ALB
-
ORD
1 stop5h 32m
American Airlines
Tue 6/238:54 pm
ORD
-
ALB
Nonstop2h 18m
American Airlines
Deal found 5/10$315
This Southwest deal was found by Cheapflights users on 5/13. 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.
Tue 10/206:20 pm
ALB
-
MDW
Nonstop2h 05m
Southwest
Sat 10/249:10 am
MDW
-
ALB
1 stop3h 40m
Southwest
Deal found 5/13$318
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:13 pm
ALB
-
ORD
Nonstop2h 47m
American Airlines
Mon 8/174:24 pm
ORD
-
ALB
Nonstop2h 16m
American Airlines
Deal found 5/13$319
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/96:55 pm
ALB
-
MDW
Nonstop2h 20m
Southwest
Tue 6/167:50 am
MDW
-
ALB
2 stops5h 40m
Southwest
Deal found 5/12$320
This Southwest deal was found by Cheapflights users on 5/14. 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 6/85:55 pm
ALB
-
MDW
1 stop5h 05m
Southwest
Tue 6/97:45 am
MDW
-
ALB
Nonstop2h 00m
Southwest
Deal found 5/14$322
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:44 am
ALB
-
ORD
1 stop6h 56m
American Airlines
Thu 6/48:54 pm
ORD
-
ALB
Nonstop2h 18m
American Airlines
Deal found 5/12$323
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 6/305:45 am
ALB
-
ORD
1 stop5h 46m
Delta
Wed 7/85:35 pm
ORD
-
ALB
1 stop4h 42m
Delta
Deal found 5/11$324
This Delta deal was found by Cheapflights users on 5/10. 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 6/175:45 am
ALB
-
ORD
1 stop4h 29m
Delta
Tue 6/235:22 pm
ORD
-
ALB
1 stop5h 02m
Delta
Deal found 5/10$325
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 8/46:00 am
ALB
-
MDW
1 stop4h 17m
Delta
Wed 8/56:42 pm
MDW
-
ALB
1 stop3h 34m
Delta
Deal found 5/11$325
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:30 am
ALB
-
ORD
Nonstop2h 44m
American Airlines
Sun 6/218:54 pm
ORD
-
ALB
Nonstop2h 18m
American Airlines
Deal found 5/13$327
This Southwest deal was found by Cheapflights users on 5/13. 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 6/103:05 pm
ALB
-
MDW
Nonstop2h 15m
Southwest
Mon 6/151:00 pm
MDW
-
ALB
Nonstop1h 50m
Southwest
Deal found 5/13$327

Find flight deals from Albany to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Albany (ALB) to Chicago (CHI). 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 May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$312
(American Airlines)

One-way from

$129
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$334

Good round-trip deal

$405 or less

Good one-way deal

$211 or less
Provider with most accurate pricing for Albany Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Albany Intl-Chicago (CHI) flights.
Search Deals
From Albany Intl to Chicago (CHI)
Search Deals
One-way flight from Albany Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Albany Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Albany Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Albany to Chicago 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 May 15, 2026.
Use the filters below to find and compare flights from Albany to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 6/20

6:10 pm-7:30 pm

Nonstop2h 20m

Chicago Midway

Tue 6/23

7:45 am-10:45 am

Nonstop2h 00m

$327

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 8/5

6:00 am-11:50 am

2 stops6h 50m

Chicago Midway

Wed 8/5

12:50 pm-9:00 pm

2 stops7h 10m

$335

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 7/15

6:05 am-9:08 am

1 stop4h 03m

Chicago Midway

Sat 7/18

6:35 pm-11:21 pm

1 stop3h 46m

$347

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 6/23

6:00 am-11:00 am

1 stop6h 00m

Chicago Midway

Fri 6/26

5:20 pm-11:45 pm

1 stop5h 25m

$347

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Thu 8/6

6:10 am-7:47 am

Nonstop2h 37m

Chicago O'Hare Intl

Sun 8/9

7:25 am-10:38 am

Nonstop2h 13m

$349
Quickest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 8/6

11:50 am-12:55 pm

Nonstop2h 05m

Chicago Midway

Sun 8/9

9:25 am-12:20 pm

Nonstop1h 55m

$349

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Fri 7/31

7:15 pm-8:30 pm

Nonstop2h 15m

Chicago Midway

Mon 8/3

7:45 am-10:45 am

Nonstop2h 00m

$349

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 6/23

6:00 am-11:00 am

1 stop6h 00m

Chicago Midway

Thu 6/25

8:55 pm-9:15 am

1 stop11h 20m

$352

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Fri 8/7

6:00 am-9:17 am

1 stop4h 17m

Chicago Midway

Mon 8/10

5:10 pm-11:57 pm

1 stop5h 47m

$354

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 6/17

11:20 am-5:55 pm

1 stop7h 35m

Chicago Midway

Wed 6/24

7:45 am-10:45 am

Nonstop2h 00m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 46 resultsSorted by cheapest first
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Compare providers for flights from Albany to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Albany to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Albany, New York-Chicago 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Albany, New York-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Albany, New York-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How far ahead should I book a flight from Albany, New York to Chicago?

The price you pay for your flight from Albany, New York to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 50 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Albany, New York to Chicago?

Currently, August is the cheapest month in which you can book a flight from Albany, New York to Chicago (average of $126). Flying from Albany, New York to Chicago in March is currently the most expensive (average of $247). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

Find hourly flight availability from Albany to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 15, 2026.

A simple way to save on the total cost of your ticket is to fly from Albany, New York to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Albany, New York to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Albany to Chicago. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Albany, New York to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Albany, New York to Chicago

Explore weekly flight availability from Albany to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 15, 2026.

The most flights from ALB to CHI are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 15, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Albany to Chicago 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
4,299 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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
4,299 reviews
Southwest
8.0
Very good
4,299 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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.
United Airlines
7.4
Good
9,717 reviews
Southwest
8.0
Very good
4,299 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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.
American Airlines
7.1
Good
11,662 reviews
Southwest
8.0
Very good
4,299 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

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 Chicago. 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?

    For a flight from Albany to Chicago, 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 26 outbound flights to Chicago per day. 3 airlines have flights to Chicago from Albany Intl on a regular basis.

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

    There are many flights that can get you from Albany, New York to Chicago in 2h 20m. Fly via Southwest, Delta, or United Airlines to get the fastest option. The distance between Albany, New York and Chicago is about 715 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Albany, New York to Chicago round-trip?

    American Airlines, at $231, was found to be the cheapest airline from Albany, New York to Chicago.Alternate airlines to your destination round-trip include United Airlines and Southwest. You may be able to fly from Albany, New York to Chicago for 31% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Albany, New York to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $112. Users have also found prices from $120 and $124 on American Airlines and United Airlines, respectively.

  • What are the most reliable airlines from Albany, New York to Chicago?

    Consider SkyWest Airlines (94%), Air Canada (80%) or ANA (79%) when booking your flight. These represent the most reliable airlines when flying from Albany, New York to Chicago.

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

    Looking at all options, your cheapest flight can be booked for $158. While the most popular route (Albany Intl - Chicago O'Hare Intl) can be booked for $305 on average, our data indicates $703 when flying from Albany, New York to Chicago.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Albany, New York to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Albany, New York to Chicago (average of $126). Flying from Albany, New York to Chicago in March is currently the most expensive (average of $247). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

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

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Top 3 airlines flying from Albany to Chicago

Discover the top 3 airlines that operate flights from Albany to Chicago. 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 May 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$231Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$243Average$380FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$266Average$364FlexibilityNo cancel feeOn-time63%

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