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Cheap Flights from Chicago Midway to New York LaGuardia

Compare Chicago Midway to New York LaGuardia flight deals

Find the cheapest month or even day of the year to fly to New York LaGuardia

Book the best New York LaGuardia fare with no extra fees

Flight deals from Chicago Midway to New York LaGuardia

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to New York LaGuardia? Find the lowest prices on one-way and return tickets right here.
New York.R 1,113 per passenger.Departing Wed, 5 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 5 Nov, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,113, select.
New York.R 1,213 per passenger.Departing Tue, 9 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 9 Dec, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,213, select.
New York.R 1,213 per passenger.Departing Wed, 1 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 1 Oct, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,213, select.
New York.R 1,213 per passenger.Departing Tue, 30 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 30 Sep, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,213, select.
New York.R 1,632 per passenger.Departing Wed, 7 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 7 Jan, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,632, select.
New York.R 1,640 per passenger.Departing Sat, 7 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 7 Feb, arriving in New York LaGuardia.Price includes taxes and charges.From R 1,640, select.
New York.R 2,086 per passenger.Departing Tue, 3 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Mar, arriving in New York LaGuardia.Price includes taxes and charges.From R 2,086, select.
New York.R 2,978 per passenger.Departing Mon, 25 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 25 Aug, arriving in New York LaGuardia.Price includes taxes and charges.From R 2,978, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to New York LaGuardia flights are currently cheapest in November.
Aug
from R 2,978
Sep
from R 1,213
Oct
from R 1,213
Nov
from R 1,113
Dec
from R 1,213
Jan
from R 1,632
Feb
from R 1,640
Mar
from R 2,086
Apr
from R 3,196
May
from R 8,190
Jun
from R 8,190
Jul
from R 8,190

Direct flights from Chicago Midway to New York LaGuardia

Chicago Midway to New York LaGuardia: Alternative routes

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

Chicago to New York: Flight information

The things to know before you go.
Cheapest flight foundR 1,113
Cheapest month to flyNovember
Average flight time2 hrs, 4 mins
Most popular airlineSouthwest Airlines
Average flights per week43

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

The best price we found for a return flight from Chicago Midway to New York LaGuardia is R 2,225. 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 4 minutes is the average flight time from Chicago Midway to New York LaGuardia.
Southwest Airlines flies direct from Chicago Midway to New York LaGuardia.
As of August 2025, there are 43 flights per week flying from Chicago Midway to New York LaGuardia.
The cheapest month to fly from Chicago Midway to New York LaGuardia is usually November.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to New York LaGuardia Airport on Monday, 10 November 2025.
Yes – the average flight time is 2 hours and 4 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 New York LaGuardia 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 New York is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to New York LaGuardia.

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

  • Book a direct flight from Chicago Midway International Airport to LaGuardia Airport and you'll be in the air for an average of 2 hours 5 minutes.

  • New York's timezone is UTC-4, which makes New York one hour ahead of Chicago.

  • Flights from MDW to LGA start from 05:10 — the first with Southwest Airlines. The last service of the day is at 20:20 with Southwest Airlines. In total, you can choose from 35 weekly Chicago Midway International Airport to LaGuardia Airport flights.

  • To ensure you get on your MDW to LGA flight, allow plenty of time to check in and drop off your luggage. Arriving two hours ahead of international departures and an hour before domestic flights is the standard rule.

  • During popular months such as July, you'll want to get to the airport earlier. Plan to arrive two hours before a domestic departure and four hours ahead of an international flight when you travel during a peak period in general.

  • Southwest Airlines is your gateway to discovering New York (and maybe even some other exciting corners of United States!). Check out the direct flights from Chicago Midway International Airport to LaGuardia Airport offered by this popular airline.

  • The majority of travellers choose to fly with Southwest Airlines on this route.

  • The most punctual carrier operating MDW to LGA flights is Southwest Airlines. Its services arrive as planned 73.06% of the time.

  • If you want to include a stop along the way, just deselect 'Direct flights only' when searching for your ticket from Chicago Midway International Airport to LaGuardia Airport. Here are the most popular stopovers between MDW and LGA:

    • Pittsburgh International Airport

    • Gerald R. Ford International Airport

    • Philadelphia International Airport

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

  • R 1,113 is currently the lowest price for a one-way Chicago Midway International Airport to LaGuardia Airport flight. Return flights start at R 2,225. These prices may change based on availability and demand.

  • Book six months before travelling. After looking at the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from MDW to LGA.

  • The cheapest month for flights from Chicago Midway International Airport to LaGuardia Airport is May. Use the 'Whole month' tool to find the lowest prices if you have a flexible travel schedule.

  • You won't have to check every day to find out if fares have gone down when you set up a Price Alert. We'll notify you the moment there's a change in price on cheap flights from MDW to LGA.

  • Find the ideal flight for you with the help of the filters. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Chicago Midway International Airport to LaGuardia Airport, use the 'Sort by' function. You can also filter results by airline, arrival and departure times, and journey duration.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • Of all flights departing from Chicago Midway International Airport, 77.88% arrive as scheduled at their destination.

  • Chicago Midway International Airport is around 19 kilometres from central Chicago. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 20 minutes or so to arrive, depending on the traffic.

  • The trip on public transport takes about 45 minutes.

  • Get your journey off to a leisurely start by staying near MDW. Whether you're taking an early flight from Chicago Midway International Airport to LaGuardia Airport or want to avoid feeling rushed, these hotels are perfect:

Arriving at LaGuardia Airport (LGA)

  • Consider booking a hotel close to LGA if you're catching a late Chicago Midway International Airport to LaGuardia Airport flight. Select one of these options and skip the long transfer after landing:

  • Go where the road takes you with a LaGuardia Airport rental car. Pick up your wheels from Dollar, Ace Rent a Car or Thrifty and venture far and wide through New York and beyond.

  • To get the best deal, book your ride from LaGuardia Airport around two weeks before your trip.

Getting from LaGuardia Airport (LGA) to central New York

  • LGA is located at Hangar 7 Centre.

  • From LaGuardia Airport, New York is approximately 18 kilometres away. It takes around 25 minutes to drive to the centre.

  • It'll take around 1 hour to get there using public transport.

When to fly to LaGuardia Airport (LGA)

  • It's time to work out your trip dates for your flight from Chicago Midway International Airport to LaGuardia Airport. July is the busiest month to visit New York. If you prefer a more laid-back vibe, go in February.

  • The warmest month in New York is July, with the temperature ranging between 18ºC (64ºF) and 30ºC (86ºF). Book your flights from Chicago Midway International Airport to LaGuardia Airport in this month if this is the type of weather you enjoy.

  • If you'd rather travel in cooler conditions, look for a cheap ticket from MDW to LGA in January. Average temperatures are between -6ºC (21ºF) and 8ºC (46ºF) then.

Explore more of United States

  • New York has its own special appeal, but there are so many other corners of United States waiting to be explored. Around 129 kilometres south-west of New York, a visit to Philadelphia will keep you busy. Start with popular sights like Liberty Bell, Independence Hall and Philadelphia Museum of Art.

  • If you're eager to discover another well-known destination in United States, consider Boston, about 306 kilometres north-east of New York. Freedom Trail, Museum of Fine Arts Boston and Boston Tea Party Ships & Museum are key reasons to visit.

Plan the rest of your trip from Chicago to New York

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.