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Cheap flights from North America to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from North America to Chicago departing on 4/16. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:09 am - 12:35 pm
DFW
-
MDW
2h 26mnonstop
Frontier Logo
8:25 am - 11:14 am
MDW
-
DFW
2h 49mnonstop
$76Frontier
Mon, Apr 27 - Thu, Apr 30
Frontier Logo
6:00 am - 7:00 am
ATL
-
MDW
2h 00mnonstop
Frontier Logo
9:16 pm - 12:30 am
MDW
-
ATL
2h 14mnonstop
$79Frontier
Mon, Jun 1 - Mon, Jun 1
Frontier Logo
7:03 pm - 8:06 pm
ATL
-
MDW
2h 03mnonstop
Frontier Logo
8:05 am - 11:15 am
MDW
-
ATL
2h 10mnonstop
$80Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
9:15 pm - 10:19 pm
ATL
-
MDW
2h 04mnonstop
Frontier Logo
6:00 am - 9:15 am
MDW
-
ATL
2h 15mnonstop
$82Frontier
Fri, Apr 10 - Sun, Apr 12
Frontier Logo
6:26 pm - 7:31 pm
ATL
-
MDW
2h 05mnonstop
Frontier Logo
2:20 pm - 5:26 pm
MDW
-
ATL
2h 06mnonstop
$84Frontier
Mon, May 11 - Wed, May 13
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
7:25 pm - 10:30 pm
MDW
-
LGA
2h 05mnonstop
$136Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
6:10 pm - 9:15 pm
MDW
-
LGA
2h 05mnonstop
$141Southwest
Wed, Apr 29 - Sat, May 2
Delta Logo
6:00 am - 8:47 am
IAD
-
MDW
3h 47m
1 stop
Delta Logo
6:38 pm - 11:03 pm
MDW
-
IAD
3h 25m
1 stop
$188Delta
Fri, Apr 17 - Mon, Apr 20
Delta Logo
12:29 pm - 5:54 pm
DCA
-
MDW
6h 25m
1 stop
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
$188Delta
Wed, Apr 8 - Fri, Apr 10
Multiple Airlines Logo
10:25 pm - 1:00 pm
IAD
-
MDW
15h 35m
2 stops
Multiple Airlines Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$197Multiple Airlines
Mon, Apr 13 - Wed, Apr 15

Frontier flights from North America to Chicago Midway Airport

Our best Frontier deals on North America to Chicago Midway Airport flight tickets
Frontier
Apr 27
DFW10:09 amDallas/Fort Worth
2h 26m
MDW12:35 pmChicago Midway
Apr 30
MDW8:25 amChicago Midway
2h 49m
DFW11:14 amDallas/Fort Worth
$76
Frontier
Jun 1
ATL6:00 amAtlanta Hartsfield-Jackson
2h 00m
MDW7:00 amChicago Midway
Jun 1
MDW9:16 pmChicago Midway
2h 14m
ATL12:30 amAtlanta Hartsfield-Jackson
$79
Frontier
May 28
ATL7:03 pmAtlanta Hartsfield-Jackson
2h 03m
MDW8:06 pmChicago Midway
Jun 1
MDW8:05 amChicago Midway
2h 10m
ATL11:15 amAtlanta Hartsfield-Jackson
$80

Southwest flights from North America to Chicago Midway Airport

Our best Southwest deals on North America to Chicago Midway Airport flight tickets
Southwest
Apr 15
LGA6:00 amNew York LaGuardia
2h 25m
MDW7:25 amChicago Midway
Apr 22
MDW7:25 pmChicago Midway
2h 05m
LGA10:30 pmNew York LaGuardia
$136
Southwest
Apr 29
LGA6:00 amNew York LaGuardia
2h 25m
MDW7:25 amChicago Midway
May 2
MDW6:10 pmChicago Midway
2h 05m
LGA9:15 pmNew York LaGuardia
$141
Southwest
Mar 31
LGA9:30 pmNew York LaGuardia
2h 30m
MDW11:00 pmChicago Midway
Apr 14
MDW9:30 amChicago Midway
2h 05m
LGA12:35 pmNew York LaGuardia
$146

momondo Fare Finder

 
Customize your flight search to find flights from North America to Chicago Midway Airport 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 February 27, 2026.
Use the filters below to find and compare flights from North America to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 4/27

10:09 am-12:35 pm

Nonstop2h 26m

Chicago Midway

Thu 4/30

8:25 am-11:14 am

Nonstop2h 49m

$76

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Mon 6/1

6:00 am-7:00 am

Nonstop2h 00m

Chicago Midway

Mon 6/1

9:16 pm-12:30 am

Nonstop2h 14m

$79

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Thu 5/28

7:03 pm-8:06 pm

Nonstop2h 03m

Chicago Midway

Mon 6/1

8:05 am-11:15 am

Nonstop2h 10m

$80

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Fri 4/10

9:15 pm-10:19 pm

Nonstop2h 04m

Chicago Midway

Sun 4/12

6:00 am-9:15 am

Nonstop2h 15m

$82

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Mon 5/11

6:26 pm-7:31 pm

Nonstop2h 05m

Chicago Midway

Wed 5/13

2:20 pm-5:26 pm

Nonstop2h 06m

$84

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 4/15

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Wed 4/22

7:25 pm-10:30 pm

Nonstop2h 05m

$136

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 4/29

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Sat 5/2

6:10 pm-9:15 pm

Nonstop2h 05m

$141

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 4/17

6:00 am-8:47 am

1 stop3h 47m

Chicago Midway

Mon 4/20

6:38 pm-11:03 pm

1 stop3h 25m

$188

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/8

12:29 pm-5:54 pm

1 stop6h 25m

Chicago Midway

Fri 4/10

6:34 pm-10:51 pm

1 stop3h 17m

$188

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

10:25 pm-1:00 pm

2 stops15h 35m

Chicago Midway

Wed 4/15

2:15 pm-12:36 am

1 stop9h 21m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from North America 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from North America, with most prices found around $149. If you are unable to visit Chicago Midway Airport during the month of January, then departing from North America during the month July is also very affordable. Most momondo users find prices during this month for around $253.

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 North America. The lowest ticket price found for a Tuesday departure recently was $254. 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 North America because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $401.

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

Flying to Chicago Midway Airport from North America in the evening is the least expensive time of day to depart. momondo users have found prices as low as $227 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $357. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

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

Cheap North America to Chicago Midway Airport flight deals and tips

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

Best Price Found

$38

Fastest flight time

0h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from North America in the past 72 hours is $38. The best round-trip flight deal from North America to Chicago Midway Airport found on momondo in the last 72 hours is $56.
The fastest flight from North America to Chicago Midway Airport takes 0h 50m
Direct flights go from North America to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from North America to Chicago Midway Airport?

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

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

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

Best airlines flying from North America to Chicago Midway Airport

Compare and see reviews for airlines that fly from North America to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $56Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $60Free CancellationRating
6.3
8,493 reviews
Search Spirit Airlines flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,242 reviews
Search Delta flights
SouthwestPriceFrom $117Free CancellationRating
8.0
4,301 reviews
Search Southwest flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,351 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from North America to Chicago. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Chicago from North America which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential North America 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 North America to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from North America are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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