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Tulum

$124+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Tulum are usually found in September or July, booked 57 days in advance, depart on a Monday or Sunday and return on a Tuesday

Cheap flight deals from Midway to Tulum

Keep the following information in mind while searching for Midway to Tulum flight deals. Data was last updated July 30, 2025.

Round-trip from

$270
(Southwest)

One-way from

$124
(Southwest)

Popular in

December

Cheapest in

September

Average price

$457
From Chicago Midway to Tulum
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One-way flight from Chicago Midway to Tulum
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Highest demand for flights based on searches. 15% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Thu 11/132:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 7/30$270
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:00 amMDW - CUN
1 stop5h 30mAeromexico
Thu 9/1112:25 pmCUN - MDW
1 stop9h 11mAeromexico
Deal found 7/29$303
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2610:35 amMDW - CUN
1 stop9h 45mDelta
Sat 11/11:58 pmCUN - MDW
1 stop8h 16mDelta
Deal found 7/28$324
This Priceline deal was found by Cheapflights users on 7/29. 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 11/86:00 amMDW - CUN
1 stop14h 20mMultiple Airlines
Sat 11/152:41 pmCUN - MDW
1 stop9h 28mMultiple Airlines
Deal found 7/29$341
This Frontier deal was found by Cheapflights users on 7/30. 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 11/86:10 amMDW - CUN
1 stop6h 16mFrontier
Sat 11/152:41 pmCUN - MDW
1 stop9h 28mFrontier
Deal found 7/30$342

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 July 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Tulum that are best for you.

Fly from

Midway

Fly to

Tulum

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 10/27

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

Sun 11/2

2:15 pm-5:00 pm

Nonstop3h 45m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/6

6:00 am-11:30 am

1 stop5h 30m

Cancun

Thu 9/11

12:25 pm-9:36 pm

1 stop9h 11m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 10/26

10:35 am-8:20 pm

1 stop9h 45m

Cancun

Sat 11/1

1:58 pm-10:14 pm

1 stop8h 16m

$324

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/4

6:15 am-12:40 pm

1 stop6h 25m

Cancun

Sat 10/11

10:50 am-12:11 am

1 stop13h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 9/11

6:20 am-12:40 pm

1 stop6h 20m

Cancun

Thu 9/18

12:25 pm-9:36 pm

1 stop9h 11m

$351

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 8/3

5:25 pm-9:00 pm

Nonstop3h 35m

$124

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/9

10:31 am-8:20 pm

1 stop9h 49m

$133

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/27

6:15 am-12:40 pm

1 stop6h 25m

$146

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 10/16

6:00 am-8:55 am

1 stop26h 55m

$147

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/7

6:00 am-2:10 pm

1 stop8h 10m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 25, 2025.

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 57 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Tulum (average of $360). Flying from Chicago Midway Airport to Tulum in March is currently the most expensive (average of $492). 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 July 30, 2025.

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 July 30, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Tulum, such as Southwest, Delta, and Aeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Tulum one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $124. Aeromexico flights start at $133 while deals on Frontier start at $146 one-way.

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

    Looking at all options, your cheapest flight can be booked for $122. While the most popular route (Chicago Midway - Cancun) can be booked for $270 on average our data indicates $271 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Tulum (average of $360). Flying from Chicago Midway Airport to Tulum in March is currently the most expensive (average of $492). 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
Midway to Cancún flights
O'Hare Intl to Cozumel flights
Midway to Cozumel flights
O'Hare Intl to Chetumal flights

Top 8 airlines flying from Midway to Tulum

Discover the top 8 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$445FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$312Average$514FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$346Average$579FlexibilityNo cancel feeOn-time63%
DeltaCheapest$380Average$610FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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