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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 7/18. 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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0 bags

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Find the cheapest flights from North America to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:00 pm - 10:02 pm
ATL
-
MDW
2h 02mnonstop
Frontier Logo
6:00 am - 9:09 am
MDW
-
ATL
2h 09mnonstop
$85Frontier
Sat, May 9 - Mon, May 11
Frontier Logo
9:00 pm - 10:02 pm
ATL
-
MDW
2h 02mnonstop
Frontier Logo
11:59 am - 3:05 pm
MDW
-
ATL
2h 06mnonstop
$86Frontier
Thu, May 14 - Sat, May 16
Frontier Logo
9:05 pm - 10:11 pm
ATL
-
MDW
2h 06mnonstop
Frontier Logo
12:27 pm - 3:41 pm
MDW
-
ATL
2h 14mnonstop
$87Frontier
Sat, Jun 27 - Tue, Jun 30
Frontier Logo
9:00 pm - 10:02 pm
ATL
-
MDW
2h 02mnonstop
Frontier Logo
12:24 pm - 3:30 pm
MDW
-
ATL
2h 06mnonstop
$88Frontier
Tue, May 12 - Tue, May 19
Southwest Logo
6:55 am - 4:35 pm
MSP
-
MDW
9h 40m
2 stops
Southwest Logo
9:05 pm - 10:35 pm
MDW
-
MSP
1h 30mnonstop
$112Southwest
Tue, May 12 - Tue, May 12
Delta Logo
7:00 am - 8:42 am
MSP
-
MDW
1h 42mnonstop
Delta Logo
9:23 am - 11:00 am
MDW
-
MSP
1h 37mnonstop
$117Delta
Tue, May 12 - Wed, May 13
Southwest Logo
7:10 am - 3:45 pm
MSP
-
MDW
8h 35m
2 stops
Southwest Logo
4:50 pm - 11:05 pm
MDW
-
MSP
6h 15m
1 stop
$122Southwest
Tue, May 12 - Tue, May 12
Delta Logo
4:20 pm - 5:56 pm
MSP
-
MDW
1h 36mnonstop
Delta Logo
7:13 pm - 8:55 pm
MDW
-
MSP
1h 42mnonstop
$147Delta
Wed, May 27 - Thu, May 28
Multiple Airlines Logo
9:13 pm - 10:02 pm
BWI
-
MDW
25h 49m
1 stop
Multiple Airlines Logo
12:04 pm - 11:29 pm
MDW
-
BWI
10h 25m
2 stops
$209Multiple Airlines
Thu, May 7 - Fri, May 15
Multiple Airlines Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Multiple Airlines Logo
2:47 pm - 2:18 pm
MDW
-
IAD
22h 31m
1 stop
$223Multiple Airlines
Tue, May 26 - Sun, May 31

Frontier flights from North America to Chicago Midway Airport

Our best Frontier deals on North America to Chicago Midway Airport flight tickets
Frontier
May 9
ATL9:00 pmAtlanta Hartsfield-Jackson
2h 02m
MDW10:02 pmChicago Midway
May 11
MDW6:00 amChicago Midway
2h 09m
ATL9:09 amAtlanta Hartsfield-Jackson
$85
Frontier
May 14
ATL9:00 pmAtlanta Hartsfield-Jackson
2h 02m
MDW10:02 pmChicago Midway
May 16
MDW11:59 amChicago Midway
2h 06m
ATL3:05 pmAtlanta Hartsfield-Jackson
$86
Frontier
Jun 27
ATL9:05 pmAtlanta Hartsfield-Jackson
2h 06m
MDW10:11 pmChicago Midway
Jun 30
MDW12:27 pmChicago Midway
2h 14m
ATL3:41 pmAtlanta Hartsfield-Jackson
$87

Southwest flights from North America to Chicago Midway Airport

Our best Southwest deals on North America to Chicago Midway Airport flight tickets
Southwest
May 12
MSP6:55 amMinneapolis St Paul
9h 40m
2 stops
MDW4:35 pmChicago Midway
May 12
MDW9:05 pmChicago Midway
1h 30m
MSP10:35 pmMinneapolis St Paul
$112
Southwest
May 12
MSP7:10 amMinneapolis St Paul
8h 35m
2 stops
MDW3:45 pmChicago Midway
May 12
MDW4:50 pmChicago Midway
6h 15m
1 stop
MSP11:05 pmMinneapolis St Paul
$122
Southwest
May 11
MSP4:25 pmMinneapolis St Paul
1h 35m
MDW6:00 pmChicago Midway
May 13
MDW7:55 amChicago Midway
1h 30m
MSP9:25 amMinneapolis St Paul
$137

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 April 21, 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

Cheapest round-trip

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Sat 5/9

9:00 pm-10:02 pm

Nonstop2h 02m

Chicago Midway

Mon 5/11

6:00 am-9:09 am

Nonstop2h 09m

$85

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Thu 5/14

9:00 pm-10:02 pm

Nonstop2h 02m

Chicago Midway

Sat 5/16

11:59 am-3:05 pm

Nonstop2h 06m

$86

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Sat 6/27

9:05 pm-10:11 pm

Nonstop2h 06m

Chicago Midway

Tue 6/30

12:27 pm-3:41 pm

Nonstop2h 14m

$87

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Tue 5/12

9:00 pm-10:02 pm

Nonstop2h 02m

Chicago Midway

Tue 5/19

12:24 pm-3:30 pm

Nonstop2h 06m

$88

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 5/12

6:55 am-4:35 pm

2 stops9h 40m

Chicago Midway

Tue 5/12

9:05 pm-10:35 pm

Nonstop1h 30m

$112

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 5/12

7:00 am-8:42 am

Nonstop1h 42m

Chicago Midway

Wed 5/13

9:23 am-11:00 am

Nonstop1h 37m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 5/12

7:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Tue 5/12

4:50 pm-11:05 pm

1 stop6h 15m

$122
Quickest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 5/27

4:20 pm-5:56 pm

Nonstop1h 36m

Chicago Midway

Thu 5/28

7:13 pm-8:55 pm

Nonstop1h 42m

$147

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 5/7

9:13 pm-10:02 pm

1 stop25h 49m

Chicago Midway

Fri 5/15

12:04 pm-11:29 pm

2 stops10h 25m

$209

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 5/26

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Sun 5/31

2:47 pm-2:18 pm

1 stop22h 31m

$223

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 February is also very affordable. Most momondo users find prices during this month for around $224.

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 $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 North America because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $382.

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 $217 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $358. 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 2 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

$61

Fastest flight time

0h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from North America in the past 72 hours is $61. The best round-trip flight deal from North America to Chicago Midway Airport found on momondo in the last 72 hours is $72.
The fastest flight from North America to Chicago Midway Airport takes 0h 45m
Direct flights go from North America to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from North America to Chicago Midway Airport

  • 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 $55Free CancellationRating
5.6
2,982 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $60Free CancellationRating
6.3
8,630 reviews
Search Spirit Airlines flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,434 reviews
Search Delta flights
JetBluePriceFrom $117Free CancellationRating
7.2
2,948 reviews
Search JetBlue flights
SouthwestPriceFrom $125Free CancellationRating
8.0
4,331 reviews
Search Southwest flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
9,613 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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