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Cheap flights from Chicago Midway Airport to North America from $31

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to North America departing on 10/24. 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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Find the cheapest flights from Chicago Midway Airport to North America

Cheap round-trip flights

Frontier Logo
4:29 pm - 6:17 pmMDW-DEN
2h 48mnonstop
Frontier Logo
7:10 pm - 10:38 pmDEN-MDW
2h 28mnonstop
$59Frontier
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Thu, Oct 23 - Mon, Oct 27
Frontier Logo
4:48 pm - 6:26 pmMDW-DEN
2h 38mnonstop
Frontier Logo
12:28 pm - 3:53 pmDEN-MDW
2h 25mnonstop
$74Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
$137Southwest
Find Deal
Mon, Sep 15 - Fri, Sep 19
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
Southwest Logo
7:30 am - 8:50 amLGA-MDW
2h 20mnonstop
$142Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
6:00 am - 12:10 pmMDW-EWR
5h 10m1 stop
Delta Logo
9:51 am - 12:28 pmEWR-MDW
3h 37m1 stop
$167Delta
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Sat, Sep 13 - Sat, Sep 20
Delta Logo
1:08 pm - 5:38 pmMDW-EWR
3h 30m1 stop
Delta Logo
1:00 pm - 6:35 pmEWR-MDW
6h 35m1 stop
$177Delta
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Sat, Sep 13 - Sat, Sep 20
Aeromexico Logo
6:00 am - 8:15 pmMDW-CUN
14h 15m1 stop
Aeromexico Logo
8:00 am - 3:26 pmCUN-MDW
7h 26m1 stop
$306Aeromexico
Find Deal
Sat, Sep 13 - Sat, Sep 20
Aeromexico Logo
6:00 am - 2:20 pmMDW-CUN
8h 20m1 stop
Aeromexico Logo
8:00 am - 9:36 pmCUN-MDW
13h 36m1 stop
$313Aeromexico
Find Deal
Sun, Sep 14 - Wed, Sep 17
Volaris Logo
8:39 pm - 9:40 amMDW-MEX
14h 01m1 stop
Volaris Logo
6:00 am - 7:16 pmMEX-MDW
12h 16m1 stop
$459Volaris
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Wed, Sep 24 - Mon, Sep 29
Volaris Logo
8:39 pm - 2:45 pmMDW-MEX
19h 06m2 stops
Volaris Logo
9:15 am - 7:16 pmMEX-MDW
9h 01m1 stop
$484Volaris
Find Deal
Thu, Sep 4 - Thu, Sep 11

Southwest flights from Chicago Midway Airport to North America

Our best Southwest deals on Chicago Midway Airport to North America flight tickets
Southwest
Sep 15
MDW2:10 pmChicago Midway
3h 00m
MIA6:10 pmMiami
Sep 19
MIA12:35 pmMiami
3h 10m
MDW2:45 pmChicago Midway
$137
Find similar
Southwest
Sep 3
MDW7:05 pmChicago Midway
2h 10m
LGA10:15 pmNew York LaGuardia
Sep 6
LGA7:30 amNew York LaGuardia
2h 20m
MDW8:50 amChicago Midway
$142
Find similar
Southwest
Sep 4
MDW5:25 amChicago Midway
8h 50m
1 stop
MIA3:15 pmMiami
Sep 7
MIA7:30 amMiami
3h 05m
MDW9:35 amChicago Midway
$147
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Delta flights from Chicago Midway Airport to North America

Our best Delta deals on Chicago Midway Airport to North America flight tickets
Delta
Sep 13
MDW6:00 amChicago Midway
5h 10m
1 stop
EWR12:10 pmNewark
Sep 20
EWR9:51 amNewark
3h 37m
1 stop
MDW12:28 pmChicago Midway
$167
Find similar
Delta
Sep 13
MDW1:08 pmChicago Midway
3h 30m
1 stop
EWR5:38 pmNewark
Sep 20
EWR1:00 pmNewark
6h 35m
1 stop
MDW6:35 pmChicago Midway
$177
Find similar
Delta
Oct 1
MDW6:00 amChicago Midway
5h 10m
1 stop
EWR12:10 pmNewark
Oct 8
EWR9:30 amNewark
3h 58m
1 stop
MDW12:28 pmChicago Midway
$179
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momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to North America that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to North America that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 10/23

4:29 pm-6:17 pm

Nonstop2h 48m

Denver Intl

Mon 10/27

7:10 pm-10:38 pm

Nonstop2h 28m

$59

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Fri 10/3

4:48 pm-6:26 pm

Nonstop2h 38m

Denver Intl

Mon 10/6

12:28 pm-3:53 pm

Nonstop2h 25m

$74

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/15

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Fri 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

New York LaGuardia

Sat 9/6

7:30 am-8:50 am

Nonstop2h 20m

$142

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 9/13

6:00 am-12:10 pm

1 stop5h 10m

Newark

Sat 9/20

9:51 am-12:28 pm

1 stop3h 37m

$167

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 9/13

1:08 pm-5:38 pm

1 stop3h 30m

Newark

Sat 9/20

1:00 pm-6:35 pm

1 stop6h 35m

$177

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/13

6:00 am-8:15 pm

1 stop14h 15m

Cancun

Sat 9/20

8:00 am-3:26 pm

1 stop7h 26m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/14

6:00 am-2:20 pm

1 stop8h 20m

Cancun

Wed 9/17

8:00 am-9:36 pm

1 stop13h 36m

$313

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Wed 9/24

8:39 pm-9:40 am

1 stop14h 01m

Mexico City Benito Juarez

Mon 9/29

6:00 am-7:16 pm

1 stop12h 16m

$459

ChicagoMexico City

MDW - MEX

MDWMEX

Chicago Midway

Thu 9/4

8:39 pm-2:45 pm

2 stops19h 06m

Mexico City Benito Juarez

Thu 9/11

9:15 am-7:16 pm

1 stop9h 01m

$484

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to North America

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 North America?

The month of February is, on average, the cheapest month to fly to North America from Chicago Midway Airport, with most prices found around $208. If you are unable to visit North America during the month of February, then departing from Chicago Midway Airport during the month September is also very affordable. Most momondo users find prices during this month for around $210.

What is the cheapest day to depart on your flight to North America?

The cheapest day to depart from Chicago Midway Airport to North America is on a Wednesday. Travelers who choose to depart for North America on a Wednesday will often find tickets for as low as $226. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to North America on Sunday is $295.

What is the cheapest time of day to depart on your flight to North America?

The cheapest time of day to fly to North America is in the evening when flights can be purchased for as low as $235. Try not to purchase tickets at noon because they tend to be around $266. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to North America flight route?

Fly from Chicago Midway to Orlando for the best Chicago Midway - North America flight prices

What cabin class options are available on Chicago Midway to North America flights?

There are 4 cabin classes available to choose from on Chicago Midway to North America 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 Chicago Midway Airport to North America flights?

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

Cheap Chicago Midway Airport to North America flight deals and tips

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

Best Price Found

$31

Fastest flight time

2h 00m

Direct flights

Every day

Airports in North America

7 airports
The best one-way flight to North America from Chicago Midway Airport in the past 72 hours is $31. The best round-trip flight deal from Chicago Midway Airport to North America found on momondo in the last 72 hours is $59.
The fastest flight from Chicago Midway Airport to North America takes 2h 00m
Direct flights go from Chicago Midway Airport to North America every day.
There are 7 airports near North America: Newark (EWR), Dallas/Fort Worth (DFW), Miami (MIA), New York LaGuardia (LGA), Orlando (MCO), Denver Intl (DEN), Las Vegas Harry Reid Intl (LAS)
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  • When did momondo last update prices for flights from Chicago Midway Airport to North America?

    Prices for flights from Chicago Midway Airport to North America refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to North America?

  • How old do you have to be to fly from Chicago Midway Airport to North America?

    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 Chicago Midway Airport to North America.

  • What documentation or ID do you need to fly to North America?

    The necessary travel and health documents for your North America 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 Chicago Midway Airport to North America?

Best airlines flying from Chicago Midway Airport to North America

Compare and see reviews for airlines that fly from Chicago Midway Airport to North America with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $50Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $63Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
DeltaPriceFrom $88Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
SouthwestPriceFrom $144Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $270Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to North America?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to North America for you.

Can I find flights from Chicago to North America with flexible booking policies on momondo?

Yes. All flights to North America from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to North America?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to North America.

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

If you are simply researching potential flights to North America, momondo offers a useful price alert feature which will track prices for flights to North America from Chicago and alert you when they change.

An easier way to manage your North America trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to North America

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Popular flights according to clicks in the last 7 days on momondo
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