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Cheap flights from Cancún 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 Cancún 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.
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Find the cheapest flights from Cancún to Chicago

Cheap round-trip flights

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
jue., ene. 15 - dom., ene. 25
Delta Logo
4:40 pm - 10:22 pm
CUN
-
MDW
6h 42m1 stop
Delta Logo
6:00 am - 4:35 pm
MDW
-
CUN
9h 35m1 stop
$278Delta
jue., ene. 22 - jue., ene. 29
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
lun., feb. 2 - lun., 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
jue., ene. 8 - dom., ene. 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
mar., may. 5 - mié., 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
lun., feb. 2 - lun., feb. 9
Delta Logo
1:40 pm - 10:22 pm
CUN
-
MDW
9h 42m1 stop
Delta Logo
11:01 am - 9:11 pm
MDW
-
CUN
9h 10m1 stop
$329Delta
mié., feb. 11 - dom., feb. 15
Delta Logo
4:40 pm - 10:22 pm
CUN
-
MDW
6h 42m1 stop
Delta Logo
6:00 am - 2:03 pm
MDW
-
CUN
7h 03m1 stop
$330Delta
mié., ene. 21 - lun., ene. 26
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
vie., mar. 13 - dom., mar. 15
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
$337Frontier
jue., ene. 8 - lun., ene. 12

Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún 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 11
CUN1:40 pmCancun
9h 42m
1 stop
MDW10:22 pmChicago Midway
Feb 15
MDW11:01 amChicago Midway
9h 10m
1 stop
CUN9:11 pmCancun
$329
Find similar

Frontier flights from Cancún to Chicago Midway Airport

Our best Frontier deals on Cancún 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
Jan 8
CUN3:14 pmCancun
8h 03m
1 stop
MDW10:17 pmChicago Midway
Jan 12
MDW6:10 amChicago Midway
6h 54m
1 stop
CUN2:04 pmCancun
$337
Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/15

4:40 pm-10:07 pm

1 stop6h 27m

Chicago Midway

dom. 1/25

6:00 am-2:03 pm

1 stop7h 03m

$277

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/22

4:40 pm-10:22 pm

1 stop6h 42m

Chicago Midway

jue. 1/29

6:00 am-4:35 pm

1 stop9h 35m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

lun. 2/2

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

lun. 2/9

6:20 am-1:47 pm

1 stop6h 27m

$285

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

dom. 1/11

6:10 am-3:05 pm

1 stop7h 55m

$314

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mar. 5/5

8:15 am-10:29 pm

1 stop14h 14m

Chicago Midway

mié. 5/13

6:00 am-11:27 pm

2 stops17h 27m

$319

CancúnChicago

CUN - MDW

CUNMDW

Cancun

lun. 2/2

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

lun. 2/9

6:54 pm-9:48 am

1 stop13h 54m

$326

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 2/11

1:40 pm-10:22 pm

1 stop9h 42m

Chicago Midway

dom. 2/15

11:01 am-9:11 pm

1 stop9h 10m

$329

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 1/21

4:40 pm-10:22 pm

1 stop6h 42m

Chicago Midway

lun. 1/26

6:00 am-2:03 pm

1 stop7h 03m

$330

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 3/13

10:39 am-6:34 pm

1 stop7h 55m

Chicago Midway

dom. 3/15

7:54 pm-9:48 am

1 stop13h 54m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

lun. 1/12

6:10 am-2:04 pm

1 stop6h 54m

$337

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 Cancún 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 Cancún. 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 Cancún 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 Cancún 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 Cancun to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Cancun to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Cancún to Chicago Midway Airport flight prices changed over time?

As of December 2025, prices for Cancún to Chicago Midway Airport flights are approximately 59% more expensive when compared to flights at the same time last year.

When to book flights from Cancún to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Cancún to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cancún to Chicago Midway Airport (CUN to MDW) flight deals and tips

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

Best Price Found

$190

Fastest flight time

3h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Cancún in the past 72 hours is $190. The best round-trip flight deal from Cancún to Chicago Midway Airport found on momondo in the last 72 hours is $358.
The fastest flight from Cancún to Chicago Midway Airport takes 3h 40m
Direct flights go from Cancún to Chicago Midway Airport every day.
Search flight deals

  • How far is Cancun to Chicago Midway by plane?

    Chicago Midway is 1425.4 mi away from Cancun. Flights usually cover this in 3h 40m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Cancun Airport to Chicago Midway Airport refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cancun Airport 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 Cancún to Chicago Midway Airport?

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
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Cancún to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

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

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

momondo provides multiple filters to help you find the best flight to Chicago from Cancún. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Cancún to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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