How long does it take to fly to Chicago Midway Airport?

On average, it takes 2h 43m to fly from United States to Chicago Midway Airport if you fly out of New York (the most popular airport in United States) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Boston and into Chicago O'Hare Intl Airport, then the flight time is around 2h 47m.

How often are flights from the United States to Chicago delayed?

Historically, on average around 20% of flights between United States and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 123 minutes.

What is the most punctual flight time for the United States to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from United States according to our data. Southwest is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 5 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 United States to Chicago Midway Airport on average per week?

209 flights are operational weekly from United States to Chicago Midway Airport as of July 2026. The most popular departure day for this route is Fri, with 26% of flights per week taking off on this day.

What is the cheapest airline that flies from United States to Chicago Midway?

Frontier, Southwest, and Delta are the most popular carriers operating from United States to Chicago Midway

Which airline has the best punctuality record on the United States to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How many flights depart from United States to Chicago Midway Airport on average per day?

29 flights are operational daily from United States to Chicago Midway Airport as of July 2026. The most popular departure time for this route is 9:00PM, with 37% of flights per day taking off in the evening.

How many operators does momondo search for flights from United States to Chicago Midway Airport?

As of July 2026, there are 4 operators available to choose from for flights from United States to Chicago Midway Airport.

How old do you have to be to fly from United States to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from United States to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$68 Cheap Flights from United States to Chicago Midway Airport in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from the United States to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from the United States to Chicago

Enter your travel dates to find the best prices.

5:25 am - 6:55 am

MSP

MDW

1h 30mnonstop

9:20 pm - 10:50 pm

MDW

MSP

1h 30mnonstop

$117Southwest

Sat, Jul 25 - Wed, Jul 29

8:00 am - 1:55 pm

MSP

MDW

5h 55m

1 stop

8:30 pm - 10:00 pm

MDW

MSP

1h 30mnonstop

$127Southwest

Tue, Aug 4 - Tue, Aug 4

7:05 am - 1:35 pm

MSP

MDW

6h 30m

2 stops

8:30 am - 10:10 am

MDW

MSP

1h 40mnonstop

$132Southwest

Tue, Jul 28 - Tue, Aug 4

6:15 am - 7:40 am

MSP

MDW

1h 25mnonstop

6:35 am - 4:10 pm

MDW

MSP

9h 35m

1 stop

$133Southwest

Wed, Aug 5 - Sat, Aug 8

8:00 am - 11:50 am

MSP

MDW

3h 50m

1 stop

4:40 pm - 10:25 pm

MDW

MSP

5h 45m

1 stop

$137Southwest

Tue, Aug 4 - Tue, Aug 4

4:24 pm - 6:01 pm

MSP

MDW

1h 37mnonstop

9:59 am - 11:42 am

MDW

MSP

1h 43mnonstop

$141Delta

Sat, Aug 8 - Mon, Aug 10

9:00 pm - 9:58 pm

ATL

MDW

1h 58mnonstop

7:25 am - 10:23 am

MDW

ATL

1h 58mnonstop

$146Frontier

Sat, Sep 19 - Sun, Sep 27

4:15 pm - 5:52 pm

MSP

MDW

1h 37mnonstop

1:51 pm - 3:35 pm

MDW

MSP

1h 44mnonstop

$147Delta

Sat, Aug 1 - Sat, Aug 8

9:59 am - 10:58 am

ATL

MDW

1h 59mnonstop

12:03 pm - 3:03 pm

MDW

ATL

2h 00mnonstop

$148Frontier

Tue, Sep 29 - Mon, Oct 5

11:05 pm - 9:51 am

SFO

MDW

8h 46m

1 stop

8:20 pm - 5:07 pm

MDW

SFO

22h 47m

2 stops

$323Multiple Airlines

Wed, Aug 5 - Sun, Aug 9

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Frontier flights from United States to Chicago Midway Airport

Our best Frontier deals on United States to Chicago Midway Airport flight tickets

Frontier

Sep 19

ATL9:00 pmAtlanta Hartsfield-Jackson

1h 58m

MDW9:58 pmChicago Midway

Sep 27

MDW7:25 amChicago Midway

1h 58m

ATL10:23 amAtlanta Hartsfield-Jackson

$146

Frontier

Sep 29

ATL9:59 amAtlanta Hartsfield-Jackson

1h 59m

MDW10:58 amChicago Midway

Oct 5

MDW12:03 pmChicago Midway

2h 00m

ATL3:03 pmAtlanta Hartsfield-Jackson

$148

Frontier

Jul 4

ATL9:05 pmAtlanta Hartsfield-Jackson

2h 06m

MDW10:11 pmChicago Midway

Jul 11

MDW12:11 pmChicago Midway

2h 02m

ATL3:13 pmAtlanta Hartsfield-Jackson

$150

Southwest flights from United States to Chicago Midway Airport

Our best Southwest deals on United States to Chicago Midway Airport flight tickets

Southwest

Jul 25

MSP5:25 amMinneapolis St Paul

1h 30m

MDW6:55 amChicago Midway

Jul 29

MDW9:20 pmChicago Midway

1h 30m

MSP10:50 pmMinneapolis St Paul

$117

Southwest

Aug 4

MSP8:00 amMinneapolis St Paul

5h 55m

1 stop

MDW1:55 pmChicago Midway

Aug 11

MDW2:20 pmChicago Midway

1h 30m

MSP3:50 pmMinneapolis St Paul

$127

Southwest

Aug 15

MSP3:20 pmMinneapolis St Paul

1h 30m

MDW4:50 pmChicago Midway

Aug 22

MDW11:45 amChicago Midway

7h 00m

2 stops

MSP6:45 pmMinneapolis St Paul

$132

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 7/25

5:25 am-6:55 am

Nonstop1h 30m

Chicago Midway

Wed 7/29

9:20 pm-10:50 pm

Nonstop1h 30m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 8/4

8:00 am-1:55 pm

1 stop5h 55m

Chicago Midway

Tue 8/4

8:30 pm-10:00 pm

Nonstop1h 30m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 7/28

7:05 am-1:35 pm

2 stops6h 30m

Chicago Midway

Tue 8/4

8:30 am-10:10 am

Nonstop1h 40m

$132

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 8/5

6:15 am-7:40 am

Nonstop1h 25m

Chicago Midway

Sat 8/8

6:35 am-4:10 pm

1 stop9h 35m

$133

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 8/4

8:00 am-11:50 am

1 stop3h 50m

Chicago Midway

Tue 8/4

4:40 pm-10:25 pm

1 stop5h 45m

$137

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 8/8

4:24 pm-6:01 pm

Nonstop1h 37m

Chicago Midway

Mon 8/10

9:59 am-11:42 am

Nonstop1h 43m

$141

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Sat 9/19

9:00 pm-9:58 pm

Nonstop1h 58m

Chicago Midway

Sun 9/27

7:25 am-10:23 am

Nonstop1h 58m

$146

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 8/1

4:15 pm-5:52 pm

Nonstop1h 37m

Chicago Midway

Sat 8/8

1:51 pm-3:35 pm

Nonstop1h 44m

$147

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Tue 9/29

9:59 am-10:58 am

Nonstop1h 59m

Chicago Midway

Mon 10/5

12:03 pm-3:03 pm

Nonstop2h 00m

$148

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 8/5

11:05 pm-9:51 am

1 stop8h 46m

Chicago Midway

Sun 8/9

8:20 pm-5:07 pm

2 stops22h 47m

$323

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from United States 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

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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 United States, with most prices found around $227. If you are unable to visit Chicago Midway Airport during the month of September, then departing from United States during the month October is also very affordable. Most momondo users find prices during this month for around $235.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from United States. The lowest ticket price found for a Tuesday departure recently was $278. 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 United States because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $403.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from United States in the evening is the least expensive time of day to depart. momondo users have found prices as low as $241 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $376. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest United States to Chicago Midway flight route?

Fly from Dallas/Fort Worth to Chicago Midway for the best United States - Chicago Midway flight prices

What cabin class options are available on United States to Chicago Midway Airport flights?

There are 4 cabin classes available to choose from on United States to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on United States to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between United States to Chicago Midway Airport.

Cheap United States to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from United States to Chicago Midway Airport

Best Price Found	$57
Fastest flight time	0h 45m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from United States in the past 72 hours is $57. The best round-trip flight deal from United States to Chicago Midway Airport found on momondo in the last 72 hours is $116.

The fastest flight from United States to Chicago Midway Airport takes 0h 45m

Direct flights go from United States to Chicago Midway Airport every day.

Search flight deals

Frequently asked questions about flying from the United States to Chicago Midway Airport

When did momondo last update prices for flights from United States to Chicago Midway Airport?
Prices for flights from United States to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from United States to Chicago Midway Airport?
As of July 2026, there are 4 operators available to choose from for flights from United States to Chicago Midway Airport.
How old do you have to be to fly from United States to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from United States to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from United States to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from United States to Chicago Midway Airport is Boeing 737 MAX 8 (21.14% of total bookings). The next most popular plane models are Boeing 737-800 (16.10%), Boeing 737-800 Passenger/BBJ2 (winglets) (11.37%), and Airbus A321neo (8.23%).

Best airlines flying from United States to Chicago Midway Airport

Compare and see reviews for airlines that fly from United States to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $55	Free Cancellation	Rating 5.6 2,846 reviews	Search Frontier flights
Delta	PriceFrom $88	Free Cancellation	Rating 7.8 8,454 reviews	Search Delta flights
JetBlue	PriceFrom $117	Free Cancellation	Rating 7.1 3,010 reviews	Search JetBlue flights
Southwest	PriceFrom $134	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest flights
United Airlines	PriceFrom $148	Free Cancellation	Rating 7.4 9,930 reviews	Search United Airlines flights

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Saint Joseph

Lansing

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Schererville

Munster

Crown Point

Monticello

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Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from United States to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from United States to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from United States to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for United States to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from United States to Chicago?

Once all potential United States to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from United States to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from United States to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Cheap flights from the United States to Chicago from $68

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the United States to Chicago departing on 9/5. 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 United States to Chicago Midway Airport

Our best Frontier deals on United States to Chicago Midway Airport flight tickets

Southwest flights from United States to Chicago Midway Airport

Our best Southwest deals on United States to Chicago Midway Airport flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from United States to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest United States to Chicago Midway flight route?

What cabin class options are available on United States to Chicago Midway Airport flights?

Can stopping save me money on United States to Chicago Midway Airport flights?

What is the cheapest airline that flies from United States to Chicago Midway?

What airlines fly to Chicago Midway Airport?

How often are flights from the United States to Chicago delayed?

What is the most punctual flight time for the United States to Chicago flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on the United States to Chicago flights?

How many flights depart from United States to Chicago Midway Airport on average per day?

How many flights depart from United States to Chicago Midway Airport on average per week?

How long does it take to fly to Chicago Midway Airport?

Cheap United States to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from United States to Chicago Midway Airport

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from the United States to Chicago Midway Airport

Best airlines flying from United States to Chicago Midway Airport

Compare and see reviews for airlines that fly from United States to Chicago Midway Airport with momondo

Traveling to a place near Chicago?

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An easier way to manage your Chicago Midway Airport trip

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