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Tulum

$115+ 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 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 Tuesday and return on a Monday

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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$252
(Southwest)

One-way from

$115
(Southwest)

Popular in

March

Cheapest in

September

Average price

$498
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
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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. 5% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/29$262
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/29$272
This Southwest deal was found by Cheapflights users on 10/30. 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.
Sun 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/30$282
This Southwest deal was found by Cheapflights users on 10/28. 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 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
Sat 11/151:00 pmCUN - MDW
1 stop6h 55mSouthwest
Deal found 10/28$287
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/38:40 amMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/72:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/28$292
This Southwest deal was found by Cheapflights users on 10/27. 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 11/18:20 amMDW - CUN
1 stop11h 30mSouthwest
Sat 11/81:50 pmCUN - MDW
1 stop6h 15mSouthwest
Deal found 10/27$296
This Southwest deal was found by Cheapflights users on 10/27. 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.
Tue 11/47:00 amMDW - CUN
1 stop9h 00mSouthwest
Thu 11/62:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/27$301
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/210:40 amMDW - CUN
Nonstop3h 45mSouthwest
Thu 11/612:55 pmCUN - MDW
2 stops8h 35mSouthwest
Deal found 10/28$302
This Southwest deal was found by Cheapflights users on 10/30. 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.
Mon 12/159:20 amMDW - CUN
1 stop10h 05mSouthwest
Thu 12/182:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/30$304

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 October 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

Tue 11/11

5:25 am-3:25 pm

1 stop9h 00m

Cancun

Sat 11/15

8:10 am-4:40 pm

1 stop9h 30m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/20

10:05 am-7:45 pm

2 stops8h 40m

Cancun

Thu 1/29

1:45 pm-4:30 pm

Nonstop3h 45m

$311

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

6:40 am-2:20 pm

1 stop6h 40m

Cancun

Fri 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$319

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

6:00 am-3:30 pm

1 stop8h 30m

Cancun

Tue 2/10

8:00 am-5:32 pm

1 stop10h 32m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Fri 1/16

4:40 pm-10:09 pm

1 stop6h 29m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/6

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Tue 2/10

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/8

9:34 am-9:11 pm

2 stops10h 37m

Cancun

Thu 1/15

12:15 pm-10:09 pm

1 stop10h 54m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 12/10

12:50 pm-9:20 pm

1 stop7h 30m

Cancun

Fri 12/12

12:00 pm-11:47 pm

1 stop12h 47m

$344

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 11/12

9:20 am-8:25 pm

1 stop10h 05m

Cancun

Sat 11/15

11:20 am-7:05 pm

2 stops8h 45m

$346

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/20

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Wed 2/25

1:40 pm-9:46 pm

1 stop9h 06m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 20 results
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 October 24, 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Tulum (average of $245). Flying from Chicago Midway Airport to Tulum in January is currently the most expensive (average of $430). 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Tulum in the afternoon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from Chicago Midway Airport to Tulum?

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 October 30, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Tulum, such as Southwest, Delta, and LATAM Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
LATAM Airlines
7.5
Good
1,873 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Aeromexico
7.4
Good
1,674 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.7
Okay
1,151 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 8h 30m. Southwest provides one of the quickest options available for as low as $326. The distance from Chicago Midway Airport to Tulum is about 1434 mi. This flight may include one or multiple stops.

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

    Looking at all options, your cheapest flight can be booked for $124. While the most popular route (Chicago Midway - Cancun) can be booked for $262 on average, our data indicates $357 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Tulum (average of $245). Flying from Chicago Midway Airport to Tulum in January is currently the most expensive (average of $430). 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

Browse thousands of different options on Cheapflights for your next trip

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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 7 airlines flying from Midway to Tulum

Discover the top 7 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$510FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$573FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$567FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$616FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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