What is the cheapest airline that flies from Chicago Midway to Mexico?

Southwest, Delta, and Aeromexico are the most popular carriers operating from Chicago Midway to Mexico

How many flights depart from Chicago Midway Airport to Mexico on average per day?

The number of flights available between Chicago Midway Airport and Mexico is 5 per day as of September 2025. The most frequent departure time is 3:00PM, with 34% of daily flights leaving in the afternoon.

What airlines fly to Mexico?

Southwest, Volaris and Delta are the top three most popular airlines that fly to Mexico from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Mexico. Keep in mind that there are 8 different airlines that fly to Mexico on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago Midway Airport to Mexico on average per week?

As of September 2025, there are 35 flights per week flying from Chicago Midway Airport to Mexico. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.

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

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

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

As of September 2025, there are 8 operators available to choose from for flights from Chicago Midway Airport to Mexico.

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

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 Mexico.

What documentation or ID do you need to fly to Mexico?

The travel and health documents required for your trip to Mexico 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 Mexico. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$119 Cheap Flights from Chicago Midway Airport to Mexico in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Mexico

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:25 am - 12:05 pmMDW-CUN

3h 40mnonstop

3:20 pm - 6:55 pmCUN-MDW

3h 35mnonstop

$261Southwest

Find Deal

Sun, Oct 26 - Thu, Oct 30

9:55 am - 1:30 pmMDW-CUN

3h 35mnonstop

12:00 pm - 3:35 pmCUN-MDW

3h 35mnonstop

$266Southwest

Find Deal

Tue, Sep 30 - Sat, Oct 4

6:00 am - 5:06 pmMDW-MTY

11h 06m1 stop

8:07 am - 11:32 pmMTY-MDW

15h 25m1 stop

$296Delta

Find Deal

Sat, Nov 15 - Sat, Nov 22

11:05 am - 11:47 pmMDW-MTY

12h 42m2 stops

8:51 am - 11:32 pmMTY-MDW

14h 41m2 stops

$301Delta

Find Deal

Sat, Nov 15 - Sat, Nov 22

11:00 am - 8:15 pmMDW-CUN

9h 15m1 stop

8:00 am - 9:10 pmCUN-MDW

13h 10m1 stop

$303Aeromexico

Find Deal

Sat, Sep 27 - Sat, Oct 4

6:00 am - 5:11 pmMDW-QRO

11h 11m1 stop

8:55 am - 3:43 pmQRO-MDW

6h 48m1 stop

$317Aeromexico

Find Deal

Sat, Nov 8 - Sat, Nov 15

6:15 am - 12:31 pmMDW-CUN

6h 16m1 stop

11:16 am - 11:20 pmCUN-MDW

12h 04m1 stop

$327Frontier

Find Deal

Mon, Oct 20 - Fri, Oct 24

2:32 pm - 6:48 pmMDW-MLM

4h 16mnonstop

9:15 am - 1:04 pmMLM-MDW

3h 49mnonstop

$336Volaris

Find Deal

Fri, Nov 14 - Wed, Nov 19

6:15 am - 12:31 pmMDW-CUN

6h 16m1 stop

11:16 am - 11:20 pmCUN-MDW

12h 04m1 stop

$337Frontier

Find Deal

Sat, Oct 25 - Mon, Oct 27

6:49 pm - 11:19 pmMDW-GDL

4h 30mnonstop

1:36 pm - 5:34 pmGDL-MDW

3h 58mnonstop

$348Volaris

Find Deal

Fri, Nov 14 - Sun, Nov 16

Frontier flights from Chicago Midway Airport to Mexico

Our best Frontier deals on Chicago Midway Airport to Mexico flight tickets

Frontier

Oct 20

MDW6:15 amChicago Midway

6h 16m

1 stop

CUN12:31 pmCancun

Oct 24

CUN11:16 amCancun

12h 04m

1 stop

MDW11:20 pmChicago Midway

$327

Find similar

Frontier

Oct 25

MDW6:15 amChicago Midway

6h 16m

1 stop

CUN12:31 pmCancun

Oct 27

CUN11:16 amCancun

12h 04m

1 stop

MDW11:20 pmChicago Midway

$337

Find similar

Frontier

Sep 25

MDW6:20 amChicago Midway

6h 20m

1 stop

CUN12:40 pmCancun

Oct 2

CUN1:55 pmCancun

9h 46m

1 stop

MDW11:41 pmChicago Midway

$384

Find similar

Southwest flights from Chicago Midway Airport to Mexico

Our best Southwest deals on Chicago Midway Airport to Mexico flight tickets

Southwest

Oct 26

MDW8:25 amChicago Midway

3h 40m

CUN12:05 pmCancun

Oct 30

CUN3:20 pmCancun

3h 35m

MDW6:55 pmChicago Midway

$261

Find similar

Southwest

Sep 30

MDW9:55 amChicago Midway

3h 35m

CUN1:30 pmCancun

Oct 4

CUN12:00 pmCancun

3h 35m

MDW3:35 pmChicago Midway

$266

Find similar

Southwest

Dec 6

MDW3:40 pmChicago Midway

3h 45m

CUN8:25 pmCancun

Dec 12

CUN2:15 pmCancun

3h 45m

MDW5:00 pmChicago Midway

$270

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 10/26

8:25 am-12:05 pm

Nonstop3h 40m

Cancun

Thu 10/30

3:20 pm-6:55 pm

Nonstop3h 35m

$261

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/30

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Sat 10/4

12:00 pm-3:35 pm

Nonstop3h 35m

$266

ChicagoMonterrey

MDW - MTY

MDWMTY

Chicago Midway

Sat 11/15

6:00 am-5:06 pm

1 stop11h 06m

Monterrey Gen Mariano Escobedo

Sat 11/22

8:07 am-11:32 pm

1 stop15h 25m

$296

ChicagoMonterrey

MDW - MTY

MDWMTY

Chicago Midway

Sat 11/15

11:05 am-11:47 pm

2 stops12h 42m

Monterrey Gen Mariano Escobedo

Sat 11/22

8:51 am-11:32 pm

2 stops14h 41m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/27

11:00 am-8:15 pm

1 stop9h 15m

Cancun

Sat 10/4

8:00 am-9:10 pm

1 stop13h 10m

$303

ChicagoSantiago de Querétaro

MDW - QRO

MDWQRO

Chicago Midway

Sat 11/8

6:00 am-5:11 pm

1 stop11h 11m

Santiago de Querétaro

Sat 11/15

8:55 am-3:43 pm

1 stop6h 48m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 10/20

6:15 am-12:31 pm

1 stop6h 16m

Cancun

Fri 10/24

11:16 am-11:20 pm

1 stop12h 04m

$327

ChicagoMorelia

MDW - MLM

MDWMLM

Chicago Midway

Fri 11/14

2:32 pm-6:48 pm

Nonstop4h 16m

Morelia

Wed 11/19

9:15 am-1:04 pm

Nonstop3h 49m

$336

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/25

6:15 am-12:31 pm

1 stop6h 16m

Cancun

Mon 10/27

11:16 am-11:20 pm

1 stop12h 04m

$337

ChicagoGuadalajara

MDW - GDL

MDWGDL

Chicago Midway

Fri 11/14

6:49 pm-11:19 pm

Nonstop4h 30m

Guadalajara Miguel Hidal

Sun 11/16

1:36 pm-5:34 pm

Nonstop3h 58m

$348

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Mexico

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

Prices

Airlines

Other information

What is the cheapest month to fly to Mexico?

If you’re not able to fly to Mexico in September, then July is your next best option. Flight prices from Chicago Midway Airport to Mexico during July average around $456.

What is the cheapest day to depart on your flight to Mexico?

The cheapest day to depart on your flight to Mexico is on a Monday when prices can be found for as low as $447. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $700. These prices are subject to change though, so be sure to set up a Price Alert for flights to Mexico.

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

Our data shows that the cheapest Chicago Midway Airport to Mexico flights are usually those with departure times in the evening. Our users have found flights to Mexico in the evening for as low as $385. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $713 on average. Flights to Mexico from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago Midway to Mexico flight route?

Fly from Chicago Midway to Guadalajara Miguel Hidal for the best Chicago Midway - Mexico flight prices

How far in advance should I book a flight to Mexico?

You are more likely to see cheaper flights to Mexico from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Mexico for around $585 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Mexico from Chicago Midway Airport for as low as $425 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway to Mexico 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 Mexico flights?

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

Cheap Chicago Midway Airport to Mexico flight deals and tips

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

Best Price Found	$124
Fastest flight time	3h 35m
Direct flights	Every day
Airports in Mexico	1 airport

The best one-way flight to Mexico from Chicago Midway Airport in the past 72 hours is $124. The best round-trip flight deal from Chicago Midway Airport to Mexico found on momondo in the last 72 hours is $280.

The fastest flight from Chicago Midway Airport to Mexico takes 3h 35m

Direct flights go from Chicago Midway Airport to Mexico every day.

There is 1 airport near Mexico: Cancun (CUN)

Search flight deals

When did momondo last update prices for flights from Chicago Midway Airport to Mexico?
Prices for flights from Chicago Midway Airport to Mexico refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Mexico?
As of September 2025, there are 8 operators available to choose from for flights from Chicago Midway Airport to Mexico.
How old do you have to be to fly from Chicago Midway Airport to Mexico?
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 Mexico.
What documentation or ID do you need to fly to Mexico?
The travel and health documents required for your trip to Mexico 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 Mexico. 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 Chicago Midway Airport to Mexico?
Based on momondo bookings for flights between Chicago Midway Airport and Mexico, the leading plane model is Airbus A320-100/200, making up 40.32% of the total bookings. Other popular models include Airbus A320neo with 28.26%, Airbus A321-100/200 with 5.92%, and Boeing 737 MAX 8 with 4.95%.

Best airlines flying from Chicago Midway Airport to Mexico

Compare and see reviews for airlines that fly from Chicago Midway Airport to Mexico with momondo

Airline	Rating	Free Cancellation	Price
Viva	PriceFrom $125	Free Cancellation	Rating 7.0 787 reviews	Search Viva flights
United Airlines	PriceFrom $161	Free Cancellation	Rating 7.4 8,929 reviews	Search United Airlines flights
Frontier	PriceFrom $200	Free Cancellation	Rating 5.8 3,172 reviews	Search Frontier flights
Volaris	PriceFrom $216	Free Cancellation	Rating 6.6 1,154 reviews	Search Volaris flights
Delta	PriceFrom $292	Free Cancellation	Rating 7.9 7,954 reviews	Search Delta flights
Aeromexico	PriceFrom $296	Free Cancellation	Rating 7.4 1,697 reviews	Search Aeromexico flights
Southwest	PriceFrom $345	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
LATAM Airlines	PriceFrom $3,369	Free Cancellation	Rating 7.5 1,847 reviews	Search LATAM Airlines flights

Why use momondo?

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

Finding the right flight to Mexico from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Mexico quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Chicago to Mexico flights to just show those with flexible booking policies.

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

Once you have performed a search for Chicago to Mexico flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Chicago to Mexico now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Mexico and let you know when they change.

An easier way to manage your Mexico 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.

Start using Trips

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Get notified when prices go down

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Find better results for your trip to Mexico

Popular cities in Mexico

Flights to Cancúnfrom $197

Flights to Mexico Cityfrom $172

Flights to Guadalajarafrom $207

Flights to Puerto Vallartafrom $253

Flights to San José del Cabofrom $166

Flights to Tijuanafrom $232

Flights to León, Guanajuatofrom $184

Flights to Oaxacafrom $252

Flights to Monterreyfrom $188

Flights to Méridafrom $159

Flights to Santiago de Querétarofrom $166

Flights to Moreliafrom $160

Cheap flights from Chicago Midway Airport to Mexico from $119

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 Mexico departing on 10/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Mexico

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Chicago Midway Airport to Mexico

Our best Frontier deals on Chicago Midway Airport to Mexico flight tickets

Southwest flights from Chicago Midway Airport to Mexico

Our best Southwest deals on Chicago Midway Airport to Mexico flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Mexico that are best for you.

See travel insights to Mexico from

How to get the cheapest flight ticket from Chicago Midway Airport to Mexico

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 Mexico?

If you’re not able to fly to Mexico in September, then July is your next best option. Flight prices from Chicago Midway Airport to Mexico during July average around $456.

What is the cheapest day to depart on your flight to Mexico?

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

What is the cheapest Chicago Midway to Mexico flight route?

Fly from Chicago Midway to Guadalajara Miguel Hidal for the best Chicago Midway - Mexico flight prices

How far in advance should I book a flight to Mexico?

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

There is only 1 cabin class available to choose from on Chicago Midway to Mexico 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 Mexico flights?

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

What is the cheapest airline that flies from Chicago Midway to Mexico?

Southwest, Delta, and Aeromexico are the most popular carriers operating from Chicago Midway to Mexico

What airlines fly to Mexico?

How many flights depart from Chicago Midway Airport to Mexico on average per day?

The number of flights available between Chicago Midway Airport and Mexico is 5 per day as of September 2025. The most frequent departure time is 3:00PM, with 34% of daily flights leaving in the afternoon.

How many flights depart from Chicago Midway Airport to Mexico on average per week?

As of September 2025, there are 35 flights per week flying from Chicago Midway Airport to Mexico. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.

Cheap Chicago Midway Airport to Mexico flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Mexico

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

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

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

What documentation or ID do you need to fly to Mexico?

What is the most popular plane model from Chicago Midway Airport to Mexico?

Best airlines flying from Chicago Midway Airport to Mexico

Compare and see reviews for airlines that fly from Chicago Midway Airport to Mexico with momondo

Why use momondo?

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

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

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

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

An easier way to manage your Mexico 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Mexico

Popular cities in Mexico

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