Route guide · 723 miles
Cheap Flights from New York to Chicago
LGA → MDW · Nonstop 1h 58m · Live round-trip fares
Looking for cheap flights from New York to Chicago? You're in the right place. Airfare Deal tracks live fares on this 723-mile route around the clock. As a rule of thumb, booking 2–4 weeks ahead lands the best prices — and a free fare alert means you never have to keep refreshing the page.
Live fares for LGA → MDW are updating. Use the search below for real-time prices.
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See live fares
Updated daily
Flight time
1h 58m
Nonstop, typical
Distance
723 mi
LGA → MDW
Cheapest month
November 2026
Fares from $111
Nonstop airlines
1
Southwest Airlines
Nonstop flights from New York to Chicago
The fastest way between the two cities is the nonstop: about 1h 58m for the 723-mile run from LGA to MDW. Those flights are flown by Southwest Airlines. Prices behave best when you book 2–4 weeks out.
Booking insights: New York → Chicago
- Distance: 723 miles · nonstop flight time: 1h 58m.
- Cheapest upcoming week in the live data starts around Nov 12, with fares from $111.
- Of the months we're tracking right now, November 2026 has the lowest fares, starting at $111.
- Fares tend to bottom out when you book about 2–4 weeks ahead — earlier than that rarely helps, later usually hurts.
- Tuesday and Wednesday departures usually undercut Friday and Sunday fares on routes like this one.
- A free fare alert beats daily checking: we watch this route and ping you when prices drop.
Price trend
Cheapest departure weeks ahead
Departing around Nov 12 is currently the cheapest window — about $42 less than the nearest weeks. Based on recent fares found for this route; prices change quickly.
Cheapest month · New York → Chicago
November 2026
Every date's recent round-trip fare, at a glance.
Fares from
$111
Cheapest: Wed, Nov 18 — $111 · Priciest: Nov 1 — $177
Get this fare →Recent fares found for specific dates in November 2026. Blank days had no recent fare in our data — ask our team and we'll check them for you.
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Flying from New York to Chicago: what you need to know
The flight
The nonstop from LGA to MDW runs about 1h 58m over 723 miles. It's a comfortable mid-range flight: long enough that seat choice matters a little, short enough that paying up for extras rarely does.
Airlines on this route
Southwest Airlines flies this route nonstop. That matters more than it sounds: the cheapest fare on one carrier is rarely the same product as the cheapest on another. Checked-bag fees, free seat selection and change rules all differ, so compare the full trip cost before you pick a winner. See our airline guides for exactly what each carrier charges — then send an enquiry and we'll confirm the all-in price for your dates.
Leaving from New York (LGA)
Plan to be at the airport two hours before a domestic departure — ninety minutes can work at smaller airports outside peak times, but security lines are the one variable you can't control. If you're checking a bag, add time rather than cutting it close. Our New York airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Chicago (MDW)
Before you land, know how you're getting from the airport to where you're staying — it's the part of the trip people forget to plan. The Chicago airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Chicago to New York fares — prices on the return direction often move on a different rhythm.
When to book
Of the months we're currently tracking, November 2026 is coming in cheapest for this route, with fares from $111. As a rule, booking 2–4 weeks ahead lands you in the sweet spot — leave it to the final two weeks and prices usually climb. If you see a fare that works, don't wait around: set a fare alert on this page and we'll watch the price for you.
Good to know before you go
- If you're traveling with only a carry-on, you can skip the bag-drop line entirely with mobile check-in.
- Download the airline's app before you fly; gate changes and delays show up there first.
- Nonstop time on this route is about 1h 58m — a one-stop itinerary needs to be a lot cheaper to be worth the extra hours.
- Tuesday and Wednesday departures are typically the cheapest days on domestic routes.
- Screenshot your fare before you enquire — prices move, and a saved fare helps our team match or beat it.
New York to Chicago flight FAQs
How long is the flight from LGA to MDW?
Nonstop flights from New York to Chicago take about 1h 58m and cover roughly 723 miles. One-stop itineraries add 2–4 hours depending on the layover city.
Are there nonstop flights from New York to Chicago?
Southwest Airlines typically operate nonstop flights from LGA to MDW. Nonstops are usually cheapest when booked 2–4 weeks ahead of departure.
What is the cheapest month to fly from New York to Chicago?
Right now, November 2026 is shaping up cheapest for New York to Chicago — we've seen fares from $111 in that month. Prices move fast, so lock in when you see a number you like.
How much are last minute flights from LGA to MDW?
Walking up to this route at the last minute is the expensive way to do it — prices inside 7 days of departure climb fast. The 2–4 weeks booking window is where the value sits.
What is a good round-trip deal from New York to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from New York to Chicago?
You'll mainly see Southwest Airlines on New York to Chicago. Checking each against the live fares below is the surest way to find the lowest price for your dates.
How early should I get to New York airport for this flight?
Plan on two hours before departure for a domestic flight — ninety minutes can work at smaller airports outside peak times. If you're checking a bag, earlier is better; the bag-drop line, not the flight, is what runs late.
Do the cheapest fares on this route include a checked bag?
Usually not. Basic economy fares on most airlines include a carry-on but charge extra for checked bags, and seat selection can cost more too. Add up the real total before comparing — a slightly higher regular fare sometimes works out cheaper. Our team confirms the full breakdown with you before you pay.
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