$108+ Cheap flights from LaGuardia, NY (LGA) 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
LGA — MDW
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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Find cheap flights from LaGuardia to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from New York LaGuardia to Chicago Midway are usually found in January or February, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Saturday
Cheap flight deals from LaGuardia to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from LaGuardia to MidwayExplore the most affordable flight options available from LaGuardia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
Explore the most affordable flight options available from LaGuardia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/9. 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 9/126:00 am -
2 stops11h 40m
Fri 9/185:50 pm -
1 stop4h 30m
Deal found 8/9![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:25 pm -
1 stop6h 10m
Tue 9/84:40 pm -
1 stop5h 35m
Deal found 8/11![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:20 am -
1 stop8h 40m
Tue 9/88:55 am -
1 stop5h 55m
Deal found 8/10![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 10/164:20 pm -
1 stop6h 40m
Sat 10/176:35 am -
2 stops15h 35m
Deal found 8/12![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/248:35 am -
1 stop7h 55m
Sun 9/275:25 am -
Nonstop2h 00m
Deal found 8/12![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:20 am -
1 stop6h 45m
Sun 9/135:25 am -
Nonstop2h 00m
Deal found 8/11![Southwest logo]()
$214
This CheapOair deal was found by Cheapflights users on 8/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am -
1 stop12h 36m
Mon 9/286:25 am -
1 stop8h 35m
Deal found 8/11![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
Nonstop2h 15m
Tue 9/17:05 pm -
Nonstop2h 05m
Deal found 8/11![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:35 pm -
1 stop8h 25m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/11![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:20 am -
1 stop8h 40m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/10![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:30 pm -
1 stop9h 50m
Fri 10/211:05 am -
1 stop6h 50m
Deal found 8/11![Southwest logo]()
$223
Best flights from LaGuardia to MidwayDiscover carefully curated flight deals from LaGuardia to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
Discover carefully curated flight deals from LaGuardia to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:20 am -
1 stop8h 40m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/11![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/109:40 am -
2 stops8h 15m
Mon 9/145:15 pm -
Nonstop2h 05m
Deal found 8/12![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/111:30 pm -
1 stop7h 40m
Sun 9/135:25 am -
Nonstop2h 00m
Deal found 8/12![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:00 pm -
1 stop5h 45m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/10![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 8/9. 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 9/1610:55 am -
Nonstop2h 20m
Sat 9/1912:10 pm -
Nonstop2h 10m
Deal found 8/9![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/9. 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 9/57:35 am -
Nonstop2h 20m
Sun 9/68:45 am -
1 stop7h 10m
Deal found 8/9![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/7. 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 10/29:00 pm -
Nonstop2h 20m
Mon 10/59:35 am -
Nonstop2h 05m
Deal found 8/7![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/7. 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 11/68:30 am -
Nonstop2h 35m
Mon 11/97:15 pm -
Nonstop2h 05m
Deal found 8/7![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/8. 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 9/112:35 pm -
1 stop5h 45m
Mon 9/147:50 pm -
Nonstop2h 05m
Deal found 8/8![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 8/8. 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 10/14:20 pm -
1 stop6h 40m
Tue 10/64:30 pm -
1 stop5h 30m
Deal found 8/8![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 8/7. 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 8/282:35 pm -
1 stop5h 45m
Sun 8/305:25 am -
Nonstop2h 00m
Deal found 8/7![Southwest logo]()
$267
Last-minute flights from LaGuardia to MidwayDiscover last-minute flight deals from LaGuardia to Midway. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from LaGuardia to Midway. Data last updated August 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am -
Nonstop2h 15m
Mon 8/315:50 pm -
1 stop4h 30m
Deal found 8/10![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
Nonstop2h 15m
Tue 9/17:05 pm -
Nonstop2h 05m
Deal found 8/11![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:25 pm -
1 stop6h 10m
Tue 9/84:40 pm -
1 stop5h 35m
Deal found 8/11![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:20 am -
1 stop8h 40m
Tue 9/88:55 am -
1 stop5h 55m
Deal found 8/10![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 8/9. 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 9/126:00 am -
2 stops11h 40m
Fri 9/185:50 pm -
1 stop4h 30m
Deal found 8/9![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:20 am -
1 stop6h 45m
Sun 9/135:25 am -
Nonstop2h 00m
Deal found 8/11![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:35 pm -
1 stop8h 25m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/11![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:20 am -
1 stop8h 40m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/10![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:25 pm -
1 stop6h 10m
Fri 10/22:40 pm -
Nonstop2h 10m
Deal found 8/11![Southwest logo]()
$213
This CheapOair deal was found by Cheapflights users on 8/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am -
1 stop12h 36m
Mon 9/286:25 am -
1 stop8h 35m
Deal found 8/12![Frontier logo]()
$217
One-way flights from LaGuardia to MidwaySearch for one-way flight options from LaGuardia to Midway. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
Search for one-way flight options from LaGuardia to Midway. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
2 stops7h 20m
Deal found 8/10![Southwest logo]()
$108
This Southwest deal was found by Cheapflights users on 8/9. 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 9/188:55 pm -
Nonstop2h 25m
Deal found 8/9![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/44:25 pm -
1 stop6h 10m
Deal found 8/12![Southwest logo]()
$112
This Southwest deal was found by Cheapflights users on 8/7. 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 9/86:00 am -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$114
This Frontier deal was found by Cheapflights users on 8/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:18 am -
1 stop5h 37m
Deal found 8/11![Frontier logo]()
$119
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/203:30 pm -
1 stop7h 30m
Deal found 8/11![Southwest logo]()
$120
This Super.com deal was found by Cheapflights users on 8/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:13 am -
1 stop5h 37m
Deal found 8/7![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:18 am -
1 stop5h 37m
Deal found 8/7![Frontier logo]()
$123
This Booking.com deal was found by Cheapflights users on 8/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:15 am -
1 stop12h 31m
Deal found 8/11![Frontier logo]()
$125
Find flight deals from LaGuardia to Midway
Discover tips and strategies to find the most affordable flight options for your journey from LaGuardia (LGA) 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 August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Southwest) |
One-way from | $108 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $406 |
Good round-trip deal | $277 or less |
Good one-way deal | $193 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from LaGuardia 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 August 12, 2026.
Use the filters below to find and compare flights from New York LaGuardia Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Sat 9/19
8:20 am-4:00 pm
1 stop8h 40m
Chicago Midway
Sun 9/20
5:25 am-8:25 am
Nonstop2h 00m
$219
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 9/10
9:40 am-4:55 pm
2 stops8h 15m
Chicago Midway
Mon 9/14
5:15 pm-8:20 pm
Nonstop2h 05m
$228
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 9/11
1:30 pm-8:10 pm
1 stop7h 40m
Chicago Midway
Sun 9/13
5:25 am-8:25 am
Nonstop2h 00m
$235
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 9/18
3:00 pm-7:45 pm
1 stop5h 45m
Chicago Midway
Sun 9/20
5:25 am-8:25 am
Nonstop2h 00m
$236
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 9/16
10:55 am-12:15 pm
Nonstop2h 20m
Chicago Midway
Sat 9/19
12:10 pm-3:20 pm
Nonstop2h 10m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Sat 9/5
7:35 am-8:55 am
Nonstop2h 20m
Chicago Midway
Sun 9/6
8:45 am-4:55 pm
1 stop7h 10m
$247
Quickest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 10/2
9:00 pm-10:20 pm
Nonstop2h 20m
Chicago Midway
Mon 10/5
9:35 am-12:40 pm
Nonstop2h 05m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 11/6
8:30 am-10:05 am
Nonstop2h 35m
Chicago Midway
Mon 11/9
7:15 pm-10:20 pm
Nonstop2h 05m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Fri 9/11
2:35 pm-7:20 pm
1 stop5h 45m
Chicago Midway
Mon 9/14
7:50 pm-10:55 pm
Nonstop2h 05m
$257
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 10/1
4:20 pm-10:00 pm
1 stop6h 40m
Chicago Midway
Tue 10/6
4:30 pm-11:00 pm
1 stop5h 30m
$267
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from LaGuardia to Midway
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 Midway in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on New York LaGuardia Airport-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 New York LaGuardia Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York LaGuardia Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New York LaGuardia Airport-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 New York LaGuardia Airport-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 LaGuardia to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from LaGuardia with our price prediction graph.
LGA-MDW
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 Midway Airport
Prices
Delays
How far ahead should I book a flight from New York LaGuardia Airport to Chicago Midway Airport?
The price you pay for your flight from New York LaGuardia Airport to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 58 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 New York LaGuardia Airport to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago Midway Airport (average of $188). Flying from New York LaGuardia Airport to Chicago Midway Airport in December is currently the most expensive (average of $410). 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 MDW?
Find hourly flight availability from LaGuardia 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 August 12, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 11% on flights from New York LaGuardia Airport to Chicago Midway Airport by exploring options for tickets in the evening.
What is the cheapest day to fly from New York LaGuardia Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from LaGuardia to Midway. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their New York LaGuardia Airport to Chicago Midway Airport 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.
How often are flights from New York to Chicago delayed?
About 23% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 137 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 at night 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, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.
The best insider tips for New York LaGuardia Airport to Chicago Midway Airport 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 Midway Airport trip
Our travel experts
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 August 12, 2026.
Get a feel of what it's like to fly with Southwest from New York LaGuardia Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from LaGuardia to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Top airline flying from LaGuardia to Midway
Discover the top airline that operate flights from LaGuardia 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 August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$164 | Average$309 | FlexibilityNo cancel fee | On-time63% |