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Tulum

$106+ Cheap flights from Midway (MDW) to Tulum, Mexico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Tulum are usually found in October or February, booked 11 days in advance, depart on a Monday or Tuesday and return on a Thursday

Cheap flight deals from Midway to Tulum

Cheapest flights from Midway to Tulum
Explore the most affordable flight options available from Midway to Tulum. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 24, 2026.

This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Thu 4/1612:04 pm
CUN
-
MDW
1 stop10h 18m
Frontier
Deal found 3/22$251
This Trip.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
-
MDW
1 stop8h 49m
Frontier
Deal found 3/21$254
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Tue 4/71:31 pm
CUN
-
MDW
1 stop8h 48m
Frontier
Deal found 3/20$257
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Sat 4/115:17 pm
CUN
-
MDW
1 stop7h 20m
Frontier
Deal found 3/23$258
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Wed 4/154:07 pm
CUN
-
MDW
1 stop27h 24m
Frontier
Deal found 3/23$260
This Travelocity deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
-
CUN
1 stop8h 46m
Frontier
Sat 5/22:09 pm
CUN
-
MDW
1 stop8h 05m
Frontier
Deal found 3/23$261
This Trip.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
-
CUN
1 stop9h 05m
Frontier
Sat 4/181:25 pm
CUN
-
MDW
1 stop8h 49m
Frontier
Deal found 3/20$265
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Mon 5/113:39 pm
CUN
-
MDW
2 stops19h 33m
Frontier
Deal found 3/20$266
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Sat 4/181:25 pm
CUN
-
MDW
1 stop8h 49m
Frontier
Deal found 3/23$271
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
MDW
-
CUN
1 stop8h 07m
Frontier
Mon 5/183:22 pm
CUN
-
MDW
1 stop19h 50m
Frontier
Deal found 3/20$274

Find flight deals from Midway to Tulum

Keep the following information in mind while searching for Midway to Tulum flight deals. Data was last updated March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(Frontier)

One-way from

$106
(Super.com)

Popular in

December

Cheapest in

October

Average price

$649
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
Search Deals
From Chicago Midway to Tulum
Search Deals
One-way flight from Chicago Midway to Tulum
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Tulum 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, Cheapflights users made 2,558,603 searches. Data last updated March 24, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Tulum that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/21

6:00 am-2:01 pm

1 stop8h 01m

Cancun

Fri 4/24

3:15 pm-10:28 pm

1 stop7h 13m

$339

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/9

6:10 am-9:45 am

Nonstop3h 35m

Cancun

Tue 5/12

3:15 pm-6:55 pm

Nonstop3h 40m

$344

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/7

6:23 am-8:16 pm

1 stop13h 53m

Cancun

Thu 5/14

3:02 pm-9:09 pm

1 stop6h 07m

$359

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/16

6:23 am-12:40 pm

1 stop6h 17m

Cancun

Tue 5/19

8:00 am-4:12 pm

1 stop8h 12m

$359
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/25

10:40 am-2:10 pm

Nonstop3h 30m

Cancun

Sat 5/2

4:00 pm-7:40 pm

Nonstop3h 40m

$365

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 4/12

6:00 am-2:08 pm

1 stop8h 08m

Cancun

Wed 4/15

1:50 pm-10:28 pm

1 stop8h 38m

$404

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 4/16

9:35 am-1:10 pm

Nonstop3h 35m

Cancun

Thu 4/23

4:10 pm-7:50 pm

Nonstop3h 40m

$422

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 4/12

6:00 am-2:08 pm

1 stop8h 08m

Cancun

Mon 4/20

8:00 am-10:28 pm

1 stop14h 28m

$422

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/23

9:22 am-8:16 pm

2 stops10h 54m

Cancun

Sat 5/30

8:00 am-6:33 pm

2 stops10h 33m

$429

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/4

7:50 am-2:10 pm

1 stop6h 20m

Cancun

Mon 5/11

4:10 pm-7:50 pm

Nonstop3h 40m

$432

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Best time to book a flight from Midway to Tulum

Have a flexible travel schedule? Discover the best time to fly to Tulum from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Tulum

How far ahead should I book a flight from Chicago Midway Airport to Tulum?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Tulum. Price data was last updated on March 13, 2026.

The price you pay for your flight from Chicago Midway Airport to Tulum may vary depending on when you book. For the best chance of a lower fare, look to book 11 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago Midway Airport to Tulum?

Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Tulum (average of $198). Flying from Chicago Midway Airport to Tulum in March is currently the most expensive (average of $402). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to TU9?

Find hourly flight availability from Midway to Tulum. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 24, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Tulum as you normally would.

Reviews of airlines servicing Tulum

Get insights into the airlines that provide service to Tulum. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tulum. Reviews last updated March 24, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Tulum, such as Southwest,Delta, andAeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,328 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,319 reviews
Southwest
8.0
Very good
4,328 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Aeromexico
7.4
Good
1,560 reviews
Southwest
8.0
Very good
4,328 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,018 reviews
Southwest
8.0
Very good
4,328 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Midway to Tulum. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Tulum?

    A quick flight from Chicago Midway Airport to Tulum can take about 3h 35m. Delta provides one of the quickest options available for as low as $344. The distance from Chicago Midway Airport to Tulum is about 1434 mi. This flight may include one or multiple stops.

  • What are the most reliable airlines from Chicago Midway Airport to Tulum?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago Midway Airport to Tulum on time: Southwest (51%), Frontier (0%), Volaris (0%).

  • What are the cheapest flights from Chicago Midway Airport to Tulum?

    Looking at all options, your cheapest flight can be booked for $144. While the most popular route (Chicago Midway - Cancun) can be booked for $278 on average, our data indicates $380 when flying from Chicago Midway Airport to Tulum.

  • Can I find deals for flights from Midway to Tulum that include hotel bookings?

    Yes. In addition to deals on Midway to Tulum flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Tulum?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Tulum.

  • Can I find deals for business class flights from Midway to Tulum?

    Yes. Cheapflights offers flight deals from Midway to Tulum by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Tulum?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Tulum (average of $198). Flying from Chicago Midway Airport to Tulum in March is currently the most expensive (average of $402). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Tulum

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Cozumel flights
Midway to Cancún flights

Top 4 airlines flying from Midway to Tulum

Discover the top 4 airlines that operate flights from Midway to Tulum. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$198Average$515FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$292Average$511FlexibilityNo cancel feeOn-time63%
AeromexicoCheapest$308Average$340FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$358Average$3,633FlexibilityNo cancel feeOn-timeN/A

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