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Cheap flights from Mexico to Chicago from $149

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Mexico to Chicago departing on 2/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Mexico to Chicago

Recent round-trip flight deals from Mexico to Chicago

Enter your travel dates to find the best prices.
Delta Logo
4:40 pm - 10:07 pm
CUN
-
MDW
6h 27m1 stop
Delta Logo
6:00 am - 2:03 pm
MDW
-
CUN
7h 03m1 stop
$277Delta
Thu, Jan 15 - Sun, Jan 25
Delta Logo
4:40 pm - 10:22 pm
CUN
-
MDW
6h 42m1 stop
Delta Logo
6:00 am - 3:30 pm
MDW
-
CUN
8h 30m1 stop
$278Delta
Thu, Jan 22 - Mon, Jan 26
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
$285Frontier
Mon, Feb 2 - Mon, Feb 9
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
6:10 am - 3:05 pm
MDW
-
CUN
7h 55m1 stop
$314Frontier
Thu, Jan 8 - Sun, Jan 11
Aeromexico Logo
8:15 am - 10:29 pm
CUN
-
MDW
14h 14m1 stop
Aeromexico Logo
6:00 am - 11:27 pm
MDW
-
CUN
17h 27m2 stops
$319Aeromexico
Tue, May 5 - Wed, May 13
Multiple Airlines Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Multiple Airlines Logo
6:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
$326Multiple Airlines
Mon, Feb 2 - Mon, Feb 9
Volaris Logo
10:39 am - 6:34 pm
CUN
-
MDW
7h 55m1 stop
Volaris Logo
7:54 pm - 9:48 am
MDW
-
CUN
13h 54m1 stop
$332Volaris
Fri, Mar 13 - Sun, Mar 15
Volaris Logo
1:39 pm - 5:34 pm
GDL
-
MDW
3h 55mnonstop
Volaris Logo
6:54 pm - 11:24 pm
MDW
-
GDL
4h 30mnonstop
$336Volaris
Sun, Feb 8 - Sun, Feb 15
Aeromexico Logo
9:56 am - 10:22 pm
BJX
-
MDW
12h 26m1 stop
Aeromexico Logo
6:00 am - 11:06 pm
MDW
-
BJX
17h 06m2 stops
$342Aeromexico
Fri, Feb 6 - Mon, Feb 9
Multiple Airlines Logo
7:00 am - 4:23 pm
MEX
-
MDW
9h 23m1 stop
Multiple Airlines Logo
9:15 am - 10:30 pm
MDW
-
MEX
13h 15m1 stop
$353Multiple Airlines
Fri, Jan 16 - Mon, Jan 19

Delta flights from Mexico to Chicago Midway Airport

Our best Delta deals on Mexico to Chicago Midway Airport flight tickets
Delta
Jan 15
CUN11:05 amCancun
6h 24m
1 stop
MDW4:29 pmChicago Midway
Jan 23
MDW12:48 pmChicago Midway
7h 23m
1 stop
CUN9:11 pmCancun
$277
Find similar
Delta
Jan 22
CUN8:00 amCancun
10h 29m
1 stop
MDW5:29 pmChicago Midway
Jan 28
MDW10:46 amChicago Midway
9h 25m
1 stop
CUN9:11 pmCancun
$278
Find similar
Delta
Feb 5
BJX12:09 pmLeón Del Bajio
10h 13m
2 stops
MDW10:22 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
15h 08m
2 stops
BJX9:08 pmLeón Del Bajio
$299
Find similar

Frontier flights from Mexico to Chicago Midway Airport

Our best Frontier deals on Mexico to Chicago Midway Airport flight tickets
Frontier
Feb 2
CUN2:57 pmCancun
8h 22m
1 stop
MDW10:19 pmChicago Midway
Feb 9
MDW6:20 amChicago Midway
6h 27m
1 stop
CUN1:47 pmCancun
$285
Find similar
Frontier
Jan 8
CUN3:14 pmCancun
8h 03m
1 stop
MDW10:17 pmChicago Midway
Jan 11
MDW6:10 amChicago Midway
7h 55m
1 stop
CUN3:05 pmCancun
$314
Find similar
Frontier
Feb 16
GDL6:10 amGuadalajara Miguel Hidal
13h 50m
1 stop
MDW8:00 pmChicago Midway
Feb 20
MDW6:54 pmChicago Midway
4h 30m
GDL11:24 pmGuadalajara Miguel Hidal
$327
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Mexico 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 December 21, 2025.
Use the filters below to find and compare flights from Mexico to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/15

4:40 pm-10:07 pm

1 stop6h 27m

Chicago Midway

Sun 1/25

6:00 am-2:03 pm

1 stop7h 03m

$277

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

4:40 pm-10:22 pm

1 stop6h 42m

Chicago Midway

Mon 1/26

6:00 am-3:30 pm

1 stop8h 30m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 2/2

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Mon 2/9

6:20 am-1:47 pm

1 stop6h 27m

$285

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Sun 1/11

6:10 am-3:05 pm

1 stop7h 55m

$314

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 5/5

8:15 am-10:29 pm

1 stop14h 14m

Chicago Midway

Wed 5/13

6:00 am-11:27 pm

2 stops17h 27m

$319

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 2/2

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Mon 2/9

6:54 pm-9:48 am

1 stop13h 54m

$326

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 3/13

10:39 am-6:34 pm

1 stop7h 55m

Chicago Midway

Sun 3/15

7:54 pm-9:48 am

1 stop13h 54m

$332

GuadalajaraChicago

GDL - MDW

GDLMDW

Guadalajara Miguel Hidal

Sun 2/8

1:39 pm-5:34 pm

Nonstop3h 55m

Chicago Midway

Sun 2/15

6:54 pm-11:24 pm

Nonstop4h 30m

$336

LeónChicago

BJX - MDW

BJXMDW

León Del Bajio

Fri 2/6

9:56 am-10:22 pm

1 stop12h 26m

Chicago Midway

Mon 2/9

6:00 am-11:06 pm

2 stops17h 06m

$342

Mexico CityChicago

MEX - MDW

MEXMDW

Mexico City Benito Juarez

Fri 1/16

7:00 am-4:23 pm

1 stop9h 23m

Chicago Midway

Mon 1/19

9:15 am-10:30 pm

1 stop13h 15m

$353

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 Mexico 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 day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Mexico. The lowest ticket price found for a Thursday departure recently was $358. 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, Tuesday is the most expensive day to depart from Mexico because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $552.

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

Flying to Chicago Midway Airport from Mexico at noon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $538. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Mexico to Chicago Midway flight route?

Fly from Cancun to Chicago Midway for the best Mexico - Chicago Midway flight prices

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

There are 2 cabin classes available to choose from on Mexico to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Mexico to Chicago Midway Airport flight deals and tips

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

Best Price Found

$168

Fastest flight time

3h 27m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Mexico in the past 72 hours is $168. The best round-trip flight deal from Mexico to Chicago Midway Airport found on momondo in the last 72 hours is $358.
The fastest flight from Mexico to Chicago Midway Airport takes 3h 27m
Direct flights go from Mexico to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Mexico to Chicago Midway Airport were last updated today.

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

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

Best airlines flying from Mexico to Chicago Midway Airport

Compare and see reviews for airlines that fly from Mexico to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $177Free CancellationRating
5.8
3,082 reviews
Search Frontier flights
VolarisPriceFrom $273Free CancellationRating
6.6
1,161 reviews
Search Volaris 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
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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 Mexico to Chicago for you.

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

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

How can momondo help me find flights from Mexico to Chicago?

momondo helps you find the best flight between Mexico and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are not ready to book a flight from Mexico 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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