When is the best time to book a flight to Midway?

Booking 57 days in advance of your planned departure date is, on average, the best time to get cheap flights to Midway. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Can I find cheaper flights to Midway if I am willing to have layovers?

Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

What is the best airline to fly to Midway?

Based on reviews from Cheapflights users, Frontier is rated the highest out of the airlines that fly to Midway.

What is the cheapest airport to fly to in Midway?

Chicago Midway is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway typically cost $25, while round-trip flights cost around $58.

How much is a round-trip flight to Midway?

A round-trip flight to Midway will typically cost around $216, however they can be found for as little as $58.

Where does the fastest flight to Midway depart from?

For those looking to save time traveling to Midway, Indianapolis offers the quickest one-way flight (0 hours 55 minutes).

Does Chicago Midway have rental cars?

Yes. Those touching down at Chicago Midway can take advantage of the rental car services offered upon their arrival.

Are there hotels close to Chicago Midway?

Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 mi away from Chicago Midway).

When is the cheapest time to fly to Midway?

Users looking for the lowest fares to Midway should consider flying on Wednesday evenings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday afternoons, when prices are usually at their highest.

What are the most popular airlines that fly to Midway?

The most popular airlines flying from New York to Midway are Southwest, Delta and Frontier.

How long is the flight to Midway?

On average, a flight from New York to Midway takes 9 hours 18 minutes. Flights to Midway from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.

What are the cheapest airlines that fly to Midway?

The cheapest airlines flying from New York to Midway are Frontier, United Airlines and Southwest.

In terms of precipitation, rainfall in Midway ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Midway when rainfall is around 1.7 in.

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Most accurate provider : Out of all of the providers offering Chicago Midway Airport flight deals, Cheapflights users have found eDreams to have the most accurate pricing on Cheapflights vs. their site about >95% of the time, users can find the same price on Chicago Midway Airport flight deals on Cheapflights and eDreams. This is based on searches made for Chicago Midway Airport flights over the past month.

Most trusted provider : eDreams is the most trusted provider by Cheapflights users offering Chicago Midway Airport flight deals. With a user feedback rating of 3 out of 3 stars (3 being the best), eDreams has received the most positive sentiment from Cheapflights users searching for flights to Chicago Midway Airport. This is based on data collected from Cheapflights searches made over the past month.

$56+ Cheap Flights to Midway

Popular in	August
Cheapest in	January
Average price	$182
Round-trip from	$85
One-way from	$56
Good round-trip deal	$157 or less
Good one-way deal	$119 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
Ovago	Price Accuracy2 stars	Trust Score*2 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars

Basic Economy on United prohibits carry-ons; exceptions for MileagePlus members or select routes.

United Economy Plus offers extra legroom seats at the front of the economy cabin.

$56+ Cheap flights to Midway

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/12. Fares are subject to change and may not be available on all flights or dates of travel.

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Flights to Midway in 2026

Find the latest flights to Midway in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on January 14, 2026.

Popular in

Cheapest in

Average price

Round-trip from

One-way from

Good round-trip deal

Good one-way deal

Find flight deals to Midway Airport

Cheapest flights to Midway AirportExplore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on January 14, 2026.

Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on January 14, 2026.

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Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Compare providers for flights to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals to Midway in January.

Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight to Chicago Midway Airport

When is the best time to book a flight to Midway?

Use this chart to determine the optimal time to book a round-trip flight from New York to Midway. Price data was last updated on January 9, 2026.

How long is the flight to Midway?

When is the cheapest time to fly to Midway?

Use this chart to determine the cheapest time to fly round-trip from New York to Midway. Price data was last updated on January 10, 2026.

What are the most popular airlines that fly to Midway?

What are the cheapest airlines that fly to Midway?

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

The best insider tips for flights to Chicago Midway Airport

AI-powered summary based on content written by travel experts. AI can make mistakes.

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport trip

Airlines

American Airlines

Frontier

Delta

United Airlines

Spirit Airlines

Allegiant Air

Airports

MDW

Our travel experts

Reviews of airlines servicing Midway

Read through reviews of airlines servicing the United States, such as Southwest, Delta, and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

FAQs about flying to Midway

Can I find cheaper flights to Midway if I am willing to have layovers?

What is the best airline to fly to Midway?

What is the cheapest airport to fly to in Midway?

How much is a round-trip flight to Midway?

Where does the fastest flight to Midway depart from?

Does Chicago Midway have rental cars?

Are there hotels close to Chicago Midway?

Traveling to a place near Chicago Midway Airport?

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Cheapest flights to Midway Airport
Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on January 14, 2026.