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Tulum

$150+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
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 Tuesday or Monday 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 May 11, 2026.

This Justfly.com deal was found by Cheapflights users on 5/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Tue 7/143:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/8$354
This Justfly.com deal was found by Cheapflights users on 5/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/7$358
This Jettzy deal was found by Cheapflights users on 5/8. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Mon 6/2910:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/8$362
This FlightHub deal was found by Cheapflights users on 5/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Mon 7/133:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/6$364
This FlightHub deal was found by Cheapflights users on 5/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:49 pm
MDW
-
CUN
1 stop13h 06m
Volaris
Thu 6/1110:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/7$365
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Fri 7/103:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/10$367
This Frontier deal was found by Cheapflights users on 5/10. 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.
Tue 7/146:00 am
MDW
-
CUN
1 stop7h 44m
Frontier
Tue 7/213:01 pm
CUN
-
MDW
1 stop7h 07m
Frontier
Deal found 5/10$368
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Wed 7/83:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/10$371
This Delta deal was found by Cheapflights users on 5/8. 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 5/176:23 am
MDW
-
CUN
2 stops13h 20m
Delta
Fri 5/221:45 pm
CUN
-
MDW
1 stop7h 24m
Delta
Deal found 5/8$376
This FlightHub deal was found by Cheapflights users on 5/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Fri 6/1910:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/8$377

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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(Justfly.com)

One-way from

$150
(eDestinos)

Popular in

May

Cheapest in

October

Average price

$618
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. 11% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 11, 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

Thu 7/30

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Thu 8/6

2:10 pm-10:36 pm

1 stop8h 26m

$398
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 7/10

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Tue 7/14

12:40 pm-7:05 pm

1 stop6h 25m

$443

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/23

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Tue 7/28

8:00 am-10:15 pm

1 stop14h 15m

$446

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 7/6

9:17 am-8:25 pm

2 stops11h 08m

Cancun

Fri 7/10

8:00 am-10:15 pm

1 stop14h 15m

$448

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 5/17

6:23 am-6:35 pm

2 stops12h 12m

Cancun

Wed 5/20

8:00 am-9:09 pm

1 stop13h 09m

$449

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/27

10:55 am-8:25 pm

1 stop9h 30m

Cancun

Sat 7/4

9:55 am-10:17 pm

1 stop12h 22m

$453

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/15

5:25 am-2:45 pm

1 stop9h 20m

Cancun

Tue 5/19

3:50 pm-9:50 pm

1 stop6h 00m

$470

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/16

6:10 am-9:45 am

Nonstop3h 35m

Cancun

Sun 5/17

11:55 am-8:35 pm

1 stop8h 40m

$472

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/16

6:23 am-8:16 pm

1 stop13h 53m

Cancun

Tue 5/19

8:08 am-9:09 pm

2 stops13h 01m

$496

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 7/5

9:17 am-8:25 pm

2 stops11h 08m

Cancun

Sun 7/12

8:00 am-4:15 pm

1 stop8h 15m

$513

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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

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 May 11, 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.

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 May 11, 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
7.9
Good
4,301 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,452 reviews
Southwest
7.9
Good
4,301 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
1,515 reviews
Southwest
7.9
Good
4,301 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
5.6
Fair
2,955 reviews
Southwest
7.9
Good
4,301 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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 $443. 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 (64%), Frontier (17%), Volaris (17%).

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

    Looking at all options, your cheapest flight can be booked for $107. While the most popular route (Chicago Midway - Cancun) can be booked for $365 on average, our data indicates $326 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.

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

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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$198Average$515FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$296Average$508FlexibilityNo cancel feeOn-time63%
AeromexicoCheapest$309Average$401FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$375Average$3,633FlexibilityNo cancel feeOn-timeN/A

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