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Cheap Flights from New York LaGuardia to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare New York LaGuardia to Chicago Midway flight deals

      Find the cheapest month or even day of the year to fly to Chicago Midway

      Book the best Chicago Midway fare with no extra fees

      Flight deals from New York LaGuardia to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from New York LaGuardia Airport to Chicago Midway Airport? If you want to travel next month, return fares start from Rs67,330. Find the lowest prices on one-way and return tickets right here.
      Chicago.Rs32,354 per passenger.Departing Tue, 22 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Tue, 22 Sep, arriving in Chicago Midway.Price includes taxes and charges.From Rs32,354, select.
      Chicago.Rs33,833 per passenger.Departing Fri, 2 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Fri, 2 Oct, arriving in Chicago Midway.Price includes taxes and charges.From Rs33,833, select.
      Chicago.Rs35,450 per passenger.Departing Thu, 12 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From Rs35,450, select.
      Chicago.Rs35,782 per passenger.Departing Sat, 5 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from New York LaGuardia on Sat, 5 Dec, arriving in Chicago Midway.Price includes taxes and charges.From Rs35,782, select.
      Chicago.Rs36,910 per passenger.Departing Tue, 13 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 13 Apr, arriving in Chicago Midway.Price includes taxes and charges.From Rs36,910, select.
      Chicago.Rs36,910 per passenger.Departing Mon, 11 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Mon, 11 Jan, arriving in Chicago Midway.Price includes taxes and charges.From Rs36,910, select.
      Chicago.Rs36,910 per passenger.Departing Thu, 4 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Thu, 4 Feb, arriving in Chicago Midway.Price includes taxes and charges.From Rs36,910, select.
      Chicago.Rs36,994 per passenger.Departing Fri, 13 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Fri, 13 Nov, arriving in Chicago Midway.Price includes taxes and charges.From Rs36,994, select.
      Chicago.Rs36,994 per passenger.Departing Tue, 11 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 11 May, arriving in Chicago Midway.Price includes taxes and charges.From Rs36,994, select.
      Chicago.Rs36,994 per passenger.Departing Fri, 4 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Fri, 4 Dec, arriving in Chicago Midway.Price includes taxes and charges.From Rs36,994, select.
      Chicago.Rs37,003 per passenger.Departing Tue, 2 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 2 Mar, arriving in Chicago Midway.Price includes taxes and charges.From Rs37,003, select.
      Chicago.Rs37,003 per passenger.Departing Fri, 30 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Fri, 30 Oct, arriving in Chicago Midway.Price includes taxes and charges.From Rs37,003, select.
      Chicago.Rs37,023 per passenger.Departing Tue, 29 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 29 Sep, arriving in Chicago Midway.Price includes taxes and charges.From Rs37,023, select.
      Chicago.Rs42,294 per passenger.Departing Tue, 1 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from New York LaGuardia on Tue, 1 Jun, arriving in Chicago Midway.Price includes taxes and charges.From Rs42,294, select.
      Chicago.Rs130,591 per passenger.Departing Wed, 14 Jul.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from New York LaGuardia on Wed, 14 Jul, arriving in Chicago Midway.Price includes taxes and charges.From Rs130,591, select.

      Find the cheapest month to fly from New York LaGuardia to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like New York LaGuardia to Chicago Midway flights are currently cheapest in September.
      Sep
      from Rs32,354
      Oct
      from Rs33,833
      Nov
      from Rs35,450
      Dec
      from Rs35,782
      Jan
      from Rs36,910
      Feb
      from Rs36,910
      Mar
      from Rs37,003
      Apr
      from Rs36,910
      May
      from Rs36,994
      Jun
      from Rs42,294
      Jul
      from Rs130,591
      Aug
      Find prices

      Direct flights from New York LaGuardia to Chicago Midway

      Southwest Airlines

      New York LaGuardia to Chicago Midway: Alternative routes

      Compare routes from New York LaGuardia to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

      Chicago Midway

      14km from central Chicago
      Closest
      from Rs32,354
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from Rs30,756
      Search flights

      Chicago Rockford

      127km from central Chicago
      from Rs40,277
      Search flights

      New York to Chicago: Flight information

      The things to know before you go.
      Cheapest flight foundRs32,354
      Cheapest month to flySeptember
      Average flight time2 hrs, 30 mins
      Most popular airlineSouthwest Airlines
      Average flights per week50

      Finding cheap flights from New York LaGuardia to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from New York LaGuardia to Chicago Midway is Rs61,553. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      2 hours and 30 minutes is the average flight time from New York LaGuardia to Chicago Midway.
      Southwest Airlines flies direct from New York LaGuardia to Chicago Midway.
      As of September 2026, there are 50 flights per week flying from New York LaGuardia to Chicago Midway.
      The cheapest month to fly from New York LaGuardia to Chicago Midway is usually September.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from New York LaGuardia Airport to Chicago Midway Airport on Tuesday, 22 September 2026.
      Yes – the average flight time is 2 hours and 30 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

      Flying from New York LaGuardia Airport (LGA) to Chicago Midway Airport (MDW): what you need to know

      • Take a direct flight from New York LaGuardia Airport to Chicago Midway Airport and you'll be in the air for an average of 2 hours 30 minutes.

      • Chicago is one hour behind New York and follows the UTC-6 timezone.

      • Every week, there are 27 New York LaGuardia Airport to Chicago Midway Airport flights. If you want to jet off early, go for the 06:00 Southwest Airlines flight. If you're eager to make the most of your time before you fly, the last flight is at 21:50 with Southwest Airlines.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules worth sticking to. Be at the airport on time to catch your LGA to MDW flight.

      • Travelling during a peak time like July? Major public holidays and other high seasons can mean longer queues and delays at security. Play it safe and get there up to four hours ahead of international flights and two hours before a domestic departure.

      • Southwest Airlines offers direct flights from New York LaGuardia Airport to Chicago Midway Airport. Book with this popular airline, then get ready to discover the sights in Chicago — and maybe even more of the United States if time allows.

      • The airline that passengers book most often on this route is Southwest Airlines.

      • With 65.72% of services arriving as planned, Southwest Airlines is the most punctual carrier offering LGA to MDW flights.

      • We make it simple to book a flight with a stopover. To see your options for tickets from New York LaGuardia Airport to Chicago Midway Airport, uncheck 'Direct flights only.' Then, choose a flight offering a stop long enough to visit your chosen city. Popular stopovers between LGA and MDW include:

        • Detroit Wayne County Airport

        • Pittsburgh International Airport

        • Port Columbus Airport

      How to find the cheapest flights from New York LaGuardia Airport (LGA) to Chicago Midway Airport (MDW)

      • Rs32,354 is currently the best price for a one-way New York LaGuardia Airport to Chicago Midway Airport flight. Return flights start from Rs61,553. These prices can change based on demand and availability.

      • To get your hands on cheap tickets from LGA to MDW, book ahead. Airlines tend to offer lower fares when flights are first released.

      • The cheapest month for flights from New York LaGuardia Airport to Chicago Midway Airport is May. Use the 'Whole month' tool to find the lowest airfares if you have flexible dates.

      • Landing cheap flights from LGA to MDW is a cinch with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know as soon as a new discounted fare appears.

      • Choose your preferred arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from New York LaGuardia Airport to Chicago Midway Airport.

      Handy information about New York LaGuardia Airport (LGA)

      • The address for LGA is Hangar 7 Centre.

      • When it comes to the on-time performance of New York LaGuardia Airport, 69% of flights complete their journey on time.

      • Central New York to New York LaGuardia Airport is approximately 13 kilometres. Depending on traffic, it'll take you about 30 minutes to get there if you're driving, ride-sharing or catching a taxi.

      • Expect a journey time of around 55 minutes when using public transport.

      • Get your break off to a leisurely start by staying near LGA. Whether you're boarding an early flight from New York LaGuardia Airport to Chicago Midway Airport or just don't like being rushed, these hotels are the answer:

      Arriving at Chicago Midway Airport (MDW)

      • If you're arriving on a late New York LaGuardia Airport to Chicago Midway Airport flight, few things top the convenience of being near the terminal. Pick up your bags from the carousel and then be showered and snoozing soon after at one of these accommodation options near MDW:

      • Fast-track your adventure by picking up a Chicago Midway Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's main sights.

      • Get the best deal by reserving your vehicle from Chicago Midway Airport around four weeks before your trip.

      When to fly to Chicago Midway Airport (MDW)

      • It's time to choose your dates for your flight from New York LaGuardia Airport to Chicago Midway Airport. July is the most popular month to visit Chicago. If you like a more relaxed vibe, go in December.

      • The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Book your flights from New York LaGuardia Airport to Chicago Midway Airport in this month if you like this kind of weather.

      • Look for cheap tickets from LGA to MDW in January if you like travelling in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

      Explore more of the United States

      • Chicago has plenty going for it, but there are so many other parts of the United States waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the move. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • If you're ready to explore another well-known destination in the United States, head for Indianapolis, about 257 kilometres south-east of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key reasons to visit.

      Plan the rest of your trip from New York to Chicago

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.