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Not ready to book? to track prices.Find the cheapest flights from New York LaGuardia Airport to Chicago
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Frontier flights from New York LaGuardia Airport to Chicago Midway Airport
Our best Frontier deals on New York LaGuardia Airport to Chicago Midway Airport flight tickets
Southwest flights from New York LaGuardia Airport to Chicago Midway Airport
Our best Southwest deals on New York LaGuardia Airport to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from New York LaGuardia Airport 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 cheapest month to fly to Chicago Midway Airport?
The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from New York LaGuardia Airport, with most prices found around $206. If you are unable to visit Chicago Midway Airport during the month of September, then departing from New York LaGuardia Airport during the month February is also very affordable. Most momondo users find prices during this month for around $220.
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 LaGuardia Airport. The lowest ticket price found for a Wednesday departure recently was $259. 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 LaGuardia Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $404.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from New York LaGuardia Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $258 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $351. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest New York LaGuardia to Chicago Midway flight route?
Fly from New York LaGuardia to Chicago Midway for the best New York LaGuardia - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from New York LaGuardia Airport when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $264 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from New York LaGuardia Airport for as low as $186 on momondo.
What cabin class options are available on New York LaGuardia to Chicago Midway flights?
There are 1 cabin classes available to choose from on New York LaGuardia 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 many flights depart from New York LaGuardia Airport to Chicago Midway Airport on average per day?
The number of flights available between New York LaGuardia Airport and Chicago Midway Airport is 5 per day as of June 2025. The most frequent departure time is 6:00AM, with 43% of daily flights leaving at noon.
How many flights depart from New York LaGuardia Airport to Chicago Midway Airport on average per week?
35 flights are operational weekly from New York LaGuardia Airport to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.
When to book flights from New York LaGuardia Airport to Chicago Midway Airport
Cheap New York LaGuardia Airport to Chicago Midway Airport (LGA to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from New York LaGuardia Airport to Chicago Midway Airport
How far is New York LaGuardia to Chicago Midway by plane?
New York LaGuardia and Chicago Midway are 722.4 mi apart from one another. Typically, this will take 2h 20m by plane in normal conditions.
When did momondo last update prices for flights from New York LaGuardia Airport to Chicago Midway Airport?
Prices for flights from New York LaGuardia Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from New York LaGuardia Airport to Chicago Midway Airport?
The number of operators available for flights from New York LaGuardia Airport to Chicago Midway Airport is 1 as of June 2025.
How old do you have to be to fly from New York LaGuardia Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New York LaGuardia Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from New York LaGuardia Airport to Chicago Midway Airport?
Based on momondo bookings for flights between New York LaGuardia Airport and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 21.28% of the total bookings. Other popular models include Boeing 737-800 with 19.09%, Boeing 737-800 Passenger/BBJ2 (winglets) with 11.05%, and Airbus A321neo with 6.53%.
What is the most popular airline from New York LaGuardia Airport to Chicago Midway Airport?
Based on momondo bookings for flights between New York LaGuardia Airport and Chicago Midway Airport, the leading airline is Southwest, making up 100% of the total bookings.
Best airlines flying from New York LaGuardia Airport to Chicago Midway Airport
Compare and see reviews for airlines that fly from New York LaGuardia Airport to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $152 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From New York LaGuardia Airport to Chicago Midway Airport
Southwest flight deals from New York LaGuardia Airport to Chicago Midway Airport start from $152 round-trip. Over the 35 Southwest flights for this route in a normal week, average airfare is usually $252 round-trip - but some users have found much cheaper deals with momondo.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from New York to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from New York to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from New York to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from New York with this policy.
How can momondo help me find flights from New York to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from New York. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for New York to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.