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$104+ Cheap flights from LaGuardia, NY (LGA) 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
LGA — CHI
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
1 adult, Economy
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Cheapflights Tip: The best prices from New York LaGuardia to Chicago are usually found in January or February, booked 73 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Cheap flight deals from LaGuardia to Chicago

Cheapest flights from LaGuardia to Chicago
Explore the most affordable flight options available from LaGuardia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.

This American Airlines deal was found by Cheapflights users on 7/28. 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 9/29:24 am
LGA
-
ORD
Nonstop2h 48m
American Airlines
Wed 9/23:05 pm
ORD
-
LGA
Nonstop2h 18m
American Airlines
Deal found 7/28$202
This Delta deal was found by Cheapflights users on 7/29. 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 8/262:50 pm
LGA
-
ORD
Nonstop2h 47m
Delta
Tue 9/17:05 pm
ORD
-
LGA
Nonstop2h 29m
Delta
Deal found 7/29$207
This Southwest deal was found by Cheapflights users on 7/29. 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 9/24:10 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Wed 9/27:05 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/29$207
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 9/18:29 pm
LGA
-
ORD
Nonstop3h 01m
American Airlines
Sat 9/58:25 pm
ORD
-
LGA
Nonstop2h 20m
American Airlines
Deal found 7/30$208
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:27 pm
LGA
-
ORD
Nonstop2h 32m
United Airlines
Wed 8/268:45 am
ORD
-
LGA
1 stop4h 24m
United Airlines
Deal found 7/30$217
This Southwest deal was found by Cheapflights users on 7/28. 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 9/26:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Tue 9/85:10 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 7/28$217
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 8/297:30 am
LGA
-
ORD
Nonstop2h 44m
Delta
Mon 8/317:05 am
ORD
-
LGA
Nonstop2h 14m
Delta
Deal found 7/28$218
This Southwest deal was found by Cheapflights users on 7/28. 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 8/299:40 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Sun 8/305:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 7/28$218
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/227:21 pm
LGA
-
ORD
Nonstop2h 57m
American Airlines
Sun 8/236:00 am
ORD
-
LGA
Nonstop2h 13m
American Airlines
Deal found 7/29$221
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:27 pm
LGA
-
ORD
Nonstop2h 32m
United Airlines
Sun 8/236:00 am
ORD
-
LGA
Nonstop2h 13m
United Airlines
Deal found 7/30$222
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 8/207:25 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Tue 8/252:40 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/30$223
This Southwest deal was found by Cheapflights users on 7/29. 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 9/113:25 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Sun 9/135:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Deal found 7/29$229

Find flight deals from LaGuardia to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from LaGuardia (LGA) 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 August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(American Airlines)

One-way from

$104
(Delta)

Popular in

July

Cheapest in

January

Average price

$286

Good round-trip deal

$280 or less

Good one-way deal

$181 or less
Provider with most accurate pricing for New York LaGuardia-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York LaGuardia-Chicago (CHI) flights.
Search Deals
From New York LaGuardia to Chicago (CHI)
Search Deals
One-way flight from New York LaGuardia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from New York LaGuardia to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from New York LaGuardia to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from LaGuardia 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 August 2, 2026.
Use the filters below to find and compare flights from New York LaGuardia Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 8/22

5:55 pm-7:57 pm

Nonstop3h 02m

Chicago O'Hare Intl

Tue 9/1

6:00 am-9:09 am

Nonstop2h 09m

$207

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/2

12:05 pm-4:50 pm

1 stop5h 45m

Chicago Midway

Wed 9/2

7:05 pm-10:10 pm

Nonstop2h 05m

$217

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/26

2:30 pm-8:10 pm

1 stop6h 40m

Chicago Midway

Wed 9/2

7:05 pm-10:10 pm

Nonstop2h 05m

$217

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 8/26

4:10 pm-5:40 pm

Nonstop2h 30m

Chicago Midway

Mon 8/31

5:00 am-8:00 am

Nonstop2h 00m

$218

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/1

2:30 pm-8:10 pm

1 stop6h 40m

Chicago Midway

Tue 9/8

4:40 pm-11:15 pm

1 stop5h 35m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/1

8:50 am-3:25 pm

1 stop7h 35m

Chicago Midway

Tue 9/1

4:40 pm-11:15 pm

1 stop5h 35m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/22

8:20 am-2:05 pm

1 stop6h 45m

Chicago Midway

Sun 8/30

5:25 am-8:25 am

Nonstop2h 00m

$228

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 9/21

8:05 am-9:45 am

Nonstop2h 40m

Chicago O'Hare Intl

Fri 9/25

7:45 pm-11:10 pm

Nonstop2h 25m

$229

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/14

7:20 am-9:02 am

Nonstop2h 42m

Chicago O'Hare Intl

Sat 10/17

5:55 pm-9:16 pm

Nonstop2h 21m

$229

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 9/24

6:00 am-7:29 am

Nonstop2h 29m

Chicago O'Hare Intl

Mon 9/28

9:30 am-12:49 pm

Nonstop2h 19m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 54 resultsSorted by cheapest first
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Compare providers for flights from LaGuardia 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 LaGuardia to Chicago in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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 New York LaGuardia Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New York LaGuardia Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York LaGuardia Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York LaGuardia Airport-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 New York LaGuardia Airport-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 LaGuardia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from LaGuardia 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 New York LaGuardia Airport to Chicago

What is the cheapest month to book a flight from New York LaGuardia Airport to Chicago?

Currently, January is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago (average of $205). Flying from New York LaGuardia Airport to Chicago in June is currently the most expensive (average of $350). 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 LGA to CHI?

Find hourly flight availability from LaGuardia 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 August 2, 2026.

It’s optimal to fly from New York LaGuardia Airport to Chicago in the evening. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from New York LaGuardia Airport to Chicago

Explore weekly flight availability from LaGuardia 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 August 2, 2026.

The most flights from LGA to CHI are scheduled on a Friday (72 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (23 on average).

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

Airfare is below average for this route at the moment.
New York LaGuardia Airport to Chicago flights typically cost between $207 and $404 in September.
The cheapest round-trip price found within the last 5 days was $202 on American Airlines (Sep 2-Sep 2).

How often are flights from New York to Chicago delayed?

About 18% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 159 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

How far ahead should I book a flight from New York LaGuardia Airport to Chicago?

The best time to book flights from New York LaGuardia Airport to Chicago is 37 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from New York LaGuardia Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from LaGuardia to Chicago. Price data was last updated on August 1, 2026.

Travelers seeking maximum savings on their New York LaGuardia Airport to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for New York LaGuardia Airport to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your New York LaGuardia Airport to Chicago trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on LGA

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 August 2, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from New York LaGuardia Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,229 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Delta
7.8
Good
8,493 reviews
Southwest
8.0
Very good
4,229 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,061 reviews
Southwest
8.0
Very good
4,229 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,846 reviews
Southwest
8.0
Very good
4,229 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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

  • How long is the flight from New York LaGuardia Airport to Chicago?

    Departing from New York LaGuardia Airport to Chicago will take you 2h 40m. The distance between New York LaGuardia Airport and Chicago is about 731 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $58, Frontier will fly you from New York LaGuardia Airport to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from $118 and $148, respectively. Users have found that Frontier is 79% cheaper than the other options available to this destination.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $75. However, be on the lookout for offers from Southwest and United Airlines, as they are both options that can get you from New York LaGuardia Airport to Chicago for a low price.

  • What are the most popular routes from New York LaGuardia Airport to Chicago?

    The most popular route from New York LaGuardia Airport to Chicago is New York LaGuardia - Chicago O'Hare Intl. You may also consider New York LaGuardia - Chicago Midway or New York LaGuardia - Chicago Greater Rockford.

  • What are the most reliable airlines from New York LaGuardia Airport to Chicago?

    Before booking your flight to Chicago from New York LaGuardia Airport, check out the most reliable airlines to get you to your destination on time: Endeavor Airlines (100%), Air France (91%), Japan Airlines( 83%).

  • What are the cheapest flights from New York LaGuardia Airport to Chicago?

    Looking for the cheapest flight from New York LaGuardia Airport to Chicago? While on average our users pay $640, our data indicates the cheapest price to be $104. The most popular route (New York LaGuardia - Chicago O'Hare Intl), is priced around $207.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from LaGuardia 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 New York LaGuardia Airport to Chicago?

    Currently, January is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago (average of $205). Flying from New York LaGuardia Airport to Chicago in June is currently the most expensive (average of $350). 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
Valparaiso
Hammond
Saint Joseph
Porter

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Top 5 airlines flying from LaGuardia to Chicago

Discover the top 5 airlines that operate flights from LaGuardia 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 August 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$180FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$334FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$148Average$317FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$164Average$316FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$164Average$291FlexibilityNo cancel feeOn-time71%

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