Cheap flights from New York to Chicago from $69
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York to Chicago departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from New York to Chicago Midway Airport
Our best Frontier deals on New York to Chicago Midway Airport flight tickets
Southwest flights from New York to Chicago Midway Airport
Our best Southwest deals on New York to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from New York to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between New York and Chicago Midway Airport?
What is the cheapest month to fly to Chicago Midway Airport?
The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from New York, with most prices found around $208. If you are unable to visit Chicago Midway Airport during the month of January, then departing from New York during the month February is also very affordable. Most momondo users find prices during this month for around $221.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from New York. The lowest ticket price found for a Wednesday departure recently was $272. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $245 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $363. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest New York to Chicago Midway flight route?
Fly from New York LaGuardia to Chicago Midway for the best New York - Chicago Midway flight prices
What cabin class options are available on New York to Chicago Midway flights?
There are 1 cabin classes available to choose from on New York to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How have New York to Chicago Midway Airport flight prices changed over time?
As of April 2025, prices for New York to Chicago Midway Airport flights are approximately 12% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from New York to Chicago Midway?
Southwest, Delta, and Frontier are the most popular carriers operating from New York to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Delta and Spirit Airlines are the top three most popular airlines that fly to Chicago Midway Airport from New York according to our data. Southwest is the first choice among our users, with 65% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from New York to Chicago Midway Airport on average per day?
As of April 2025, 5 flights take off from New York and land in Chicago Midway Airport each day. The most common flight departure time for this route is 11:00AM, with 43% of daily flights taking off at noon.
How many flights depart from New York to Chicago Midway Airport on average per week?
The number of flights available between New York and Chicago Midway Airport is 37 per week as of April 2025. The most frequent departure day is Mon, with 19% of weekly flights leaving on this day.
When to book flights from New York to Chicago Midway Airport
Cheap New York to Chicago Midway Airport (NYC to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from New York to Chicago Midway Airport
How far is New York to Chicago Midway by plane?
Chicago Midway is 716.7 mi away from New York. Flights usually cover this in 2h 15m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from New York to Chicago Midway Airport?
Prices for flights from New York to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from New York to Chicago Midway Airport?
There are 3 operators available for flights from New York to Chicago Midway Airport as of April 2025.
How old do you have to be to fly from New York to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from New York to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from New York to Chicago Midway Airport is Boeing 737 MAX 8, representing 20.29% of all bookings. The subsequent popular models are Boeing 737-800 at 17.62%, Boeing 737-800 Passenger/BBJ2 (winglets) at 11.63%, and Airbus A320neo at 9.33%.
What is the most popular airline from New York to Chicago Midway Airport?
Based on momondo bookings for flights between New York and Chicago Midway Airport, the leading airline is Southwest, making up 78% of the total bookings. Other popular airlines include Delta with 8%, Spirit Airlines with 5%, and Frontier with 4%.
Best airlines flying from New York to Chicago Midway Airport
Compare and see reviews for airlines that fly from New York to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $37 | Free Cancellation | Rating 6.3 7,961 reviews | |||
| PriceFrom $148 | Free Cancellation | Rating 8.0 4,295 reviews | |||
| PriceFrom $187 | Free Cancellation | Rating 8.0 7,936 reviews |
Southwest Flights From New York to Chicago Midway Airport
Across 37 Southwest flights from New York to Chicago Midway Airport this week, the average price was $248, with the best Southwest deals starting from $148 round-trip. 4,295 users have rated Southwest on momondo, with an average score of 8.0/10.
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Why should I use momondo to find a flight deal from New York to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from New York.
Can I find flights from New York to Chicago with flexible booking policies on momondo?
All flight searches from New York to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from New York to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from New York.
I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New York and alert you when they change.