$120+ Cheap flights from Chicago (CHI) 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Aug 11 — Aug 181
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Tulum with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Tulum are usually found in January or September, booked 87 days in advance, depart on a Sunday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Tulum
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to TulumExplore the most affordable flight options available from Chicago to Tulum. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 12, 2026.
Explore the most affordable flight options available from Chicago to Tulum. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Sun 8/239:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 7/9![Volaris logo]()
$312
This FlightHub deal was found by Cheapflights users on 7/11. 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.
Wed 11/46:23 am
ORD
- CUN
1 stop13h 38m
Volaris
Fri 11/1310:20 am
CUN
- ORD
1 stop14h 19m
Volaris
Deal found 7/11![Volaris logo]()
$313
This Super.com deal was found by Cheapflights users on 7/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:59 am
ORD
- CUN
1 stop12h 07m
Volaris
Mon 8/243:55 pm
CUN
- ORD
1 stop12h 59m
Volaris
Deal found 7/10![Volaris logo]()
$314
This Justfly.com deal was found by Cheapflights users on 7/9. 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 11/46:23 am
ORD
- CUN
1 stop13h 38m
Volaris
Mon 11/96:28 pm
CUN
- ORD
1 stop11h 08m
Volaris
Deal found 7/9![Volaris logo]()
$315
This Kissandfly.com deal was found by Cheapflights users on 7/9. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:21 am
ORD
- CUN
1 stop11h 53m
Multiple Airlines
Thu 8/2710:40 am
CUN
- ORD
2 stops14h 15m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Sat 8/224:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Deal found 7/8![Volaris logo]()
$317
This FlightHub deal was found by Cheapflights users on 7/12. 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.
Thu 9/37:09 am
ORD
- CUN
1 stop10h 21m
Volaris
Sun 9/611:16 am
CUN
- ORD
1 stop12h 50m
Volaris
Deal found 7/12![Volaris logo]()
$318
This Viva deal was found by Cheapflights users on 7/8. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:40 pm
ORD
- CUN
1 stop8h 05m
Viva
Fri 10/231:10 am
CUN
- ORD
1 stop9h 50m
Viva
Deal found 7/8![Viva logo]()
$319
This Viva deal was found by Cheapflights users on 7/11. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:20 pm
ORD
- CUN
1 stop20h 35m
Viva
Sun 11/17:00 am
CUN
- ORD
1 stop16h 45m
Viva
Deal found 7/11![Viva logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/112:42 am
ORD
- CUN
1 stop12h 23m
Volaris
Thu 12/103:18 pm
CUN
- ORD
1 stop7h 48m
Volaris
Deal found 7/7![Volaris logo]()
$321
This Viva deal was found by Cheapflights users on 7/9. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:30 am
ORD
- CUN
1 stop15h 35m
Viva
Sun 12/67:00 am
CUN
- ORD
1 stop16h 50m
Viva
Deal found 7/9![Viva logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/131:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Tue 7/215:40 pm
CUN
- ORD
1 stop11h 14m
Volaris
Deal found 7/7![Volaris logo]()
$323
Best flights from Chicago to TulumDiscover carefully curated flight deals from Chicago to Tulum that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 12, 2026.
Discover carefully curated flight deals from Chicago to Tulum that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 12, 2026.
This Southwest deal was found by Cheapflights users on 7/9. 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 8/235:10 am
MDW
- CUN
1 stop6h 40m
Southwest
Sun 8/302:40 pm
CUN
- MDW
1 stop6h 30m
Southwest
Deal found 7/9![Southwest logo]()
$428
This Delta deal was found by Cheapflights users on 7/11. 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.
Tue 8/256:40 am
ORD
- CUN
2 stops12h 04m
Delta
Tue 9/16:04 am
CUN
- ORD
1 stop8h 12m
Delta
Deal found 7/11![Delta logo]()
$437
This United Airlines deal was found by Cheapflights users on 7/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:55 am
ORD
- CUN
1 stop8h 45m
United Airlines
Sat 8/293:38 pm
CUN
- ORD
Nonstop3h 57m
United Airlines
Deal found 7/10![United Airlines logo]()
$463
This Volaris deal was found by Cheapflights users on 7/11. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Tue 8/410:40 am
CUN
- MDW
1 stop8h 54m
Volaris
Deal found 7/11![Volaris logo]()
$519
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:00 am
MDW
- CUN
1 stop10h 00m
Southwest
Fri 10/231:00 pm
CUN
- MDW
1 stop9h 00m
Southwest
Deal found 7/7![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 7/9. 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.
Sat 10/108:55 am
ORD
- CUN
2 stops11h 20m
Delta
Fri 10/166:04 am
CUN
- ORD
1 stop8h 12m
Delta
Deal found 7/9![Delta logo]()
$450
This United Airlines deal was found by Cheapflights users on 7/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Sun 10/183:38 pm
CUN
- ORD
Nonstop3h 57m
United Airlines
Deal found 7/11![United Airlines logo]()
$485
This Southwest deal was found by Cheapflights users on 7/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:35 am
MDW
- CUN
2 stops9h 30m
Southwest
Wed 10/73:20 pm
CUN
- MDW
Nonstop3h 35m
Southwest
Deal found 7/10![Southwest logo]()
$454
This Delta deal was found by Cheapflights users on 7/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:35 am
MDW
- CUN
1 stop9h 35m
Delta
Tue 12/81:40 pm
CUN
- MDW
1 stop9h 30m
Delta
Deal found 7/10![Delta logo]()
$456
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:46 am
ORD
- CUN
Nonstop3h 40m
United Airlines
Tue 10/63:38 pm
CUN
- ORD
Nonstop3h 57m
United Airlines
Deal found 7/8![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 7/9. 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.
Wed 9/236:00 am
ORD
- CUN
2 stops12h 39m
Delta
Mon 9/2812:38 pm
CUN
- ORD
2 stops11h 21m
Delta
Deal found 7/9![Delta logo]()
$456
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:55 am
MDW
- CUN
Nonstop3h 45m
Southwest
Fri 11/202:10 pm
CUN
- MDW
Nonstop3h 40m
Southwest
Deal found 7/7![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 7/9. 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.
Wed 9/236:00 am
ORD
- CUN
2 stops12h 39m
Delta
Sun 9/277:56 am
CUN
- ORD
2 stops12h 59m
Delta
Deal found 7/9![Delta logo]()
$456
This Southwest deal was found by Cheapflights users on 7/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:00 pm
MDW
- CUN
2 stops19h 15m
Southwest
Fri 10/302:20 pm
CUN
- MDW
1 stop7h 05m
Southwest
Deal found 7/10![Southwest logo]()
$501
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:29 am
MDW
- CUN
2 stops10h 46m
Delta
Fri 10/168:00 am
CUN
- MDW
2 stops10h 05m
Delta
Deal found 7/7![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:00 am
MDW
- CUN
Nonstop3h 45m
Southwest
Tue 10/271:45 pm
CUN
- MDW
1 stop8h 10m
Southwest
Deal found 7/6![Southwest logo]()
$511
This Delta deal was found by Cheapflights users on 7/9. 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.
Thu 10/19:45 am
ORD
- CUN
1 stop10h 05m
Delta
Mon 10/56:04 am
CUN
- ORD
2 stops12h 41m
Delta
Deal found 7/9![Delta logo]()
$473
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:50 pm
MDW
- CUN
2 stops19h 25m
Southwest
Sun 10/412:40 pm
CUN
- MDW
2 stops8h 00m
Southwest
Deal found 7/6![Southwest logo]()
$520
This Delta deal was found by Cheapflights users on 7/11. 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.
Fri 10/96:30 am
ORD
- CUN
2 stops12h 09m
Delta
Fri 10/1612:38 pm
CUN
- ORD
1 stop11h 15m
Delta
Deal found 7/11![Delta logo]()
$482
This Delta deal was found by Cheapflights users on 7/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:59 am
ORD
- CUN
1 stop6h 02m
Delta
Tue 8/2512:38 pm
CUN
- ORD
2 stops11h 19m
Delta
Deal found 7/10![Delta logo]()
$482
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:05 am
ORD
- CUN
2 stops13h 05m
Delta
Tue 12/81:40 pm
CUN
- ORD
1 stop11h 10m
Delta
Deal found 7/7![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 7/11. 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.
Tue 9/156:05 am
MDW
- CUN
2 stops12h 34m
Delta
Sat 9/198:05 am
CUN
- MDW
1 stop7h 20m
Delta
Deal found 7/11![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
ORD
- CUN
2 stops12h 39m
Delta
Wed 9/236:04 am
CUN
- ORD
2 stops12h 41m
Delta
Deal found 7/7![Delta logo]()
$492
Last-minute flights from Chicago to TulumDiscover last-minute flight deals from Chicago to Tulum. Data last updated July 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tulum. Data last updated July 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/132:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Wed 7/229:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 7/8![Volaris logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/131:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Tue 7/215:40 pm
CUN
- ORD
1 stop11h 14m
Volaris
Deal found 7/7![Volaris logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Wed 8/196:06 pm
CUN
- ORD
1 stop11h 32m
Volaris
Deal found 7/8![Volaris logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Sat 8/224:32 pm
CUN
- ORD
1 stop12h 09m
Volaris
Deal found 7/8![Volaris logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:53 am
ORD
- CUN
1 stop9h 11m
Volaris
Fri 8/2110:50 am
CUN
- ORD
1 stop12h 57m
Volaris
Deal found 7/7![Volaris logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Thu 8/207:14 pm
CUN
- ORD
1 stop9h 27m
Volaris
Deal found 7/8![Volaris logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Mon 8/244:32 pm
CUN
- ORD
1 stop8h 23m
Volaris
Deal found 7/7![Volaris logo]()
$319
This American Airlines deal was found by Cheapflights users on 7/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:20 am
ORD
- CUN
Nonstop3h 41m
American Airlines
Thu 8/273:37 pm
CUN
- ORD
1 stop8h 15m
American Airlines
Deal found 7/9![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:59 am
ORD
- CUN
1 stop8h 32m
Volaris
Sun 8/239:50 pm
CUN
- ORD
1 stop8h 02m
Volaris
Deal found 7/9![Volaris logo]()
$312
This FlightHub deal was found by Cheapflights users on 7/9. 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.
Wed 8/191:59 am
ORD
- CUN
1 stop14h 07m
Volaris
Mon 8/2410:40 am
CUN
- ORD
1 stop14h 15m
Volaris
Deal found 7/9![Volaris logo]()
$314
This Kissandfly.com deal was found by Cheapflights users on 7/9. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:21 am
ORD
- CUN
1 stop11h 53m
Multiple Airlines
Thu 8/2710:40 am
CUN
- ORD
2 stops14h 15m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:09 am
ORD
- CUN
1 stop10h 21m
Volaris
Mon 8/313:20 pm
CUN
- ORD
1 stop8h 27m
Volaris
Deal found 7/7![Volaris logo]()
$318
One-way flights from Chicago to TulumSearch for one-way flight options from Chicago to Tulum. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
Search for one-way flight options from Chicago to Tulum. Find affordable one-way fares based on user searches. Data last updated July 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/6![Volaris logo]()
$120
This FlightHub deal was found by Cheapflights users on 7/8. 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.
Wed 11/41:19 am
ORD
- CUN
1 stop13h 01m
Volaris
Deal found 7/8![Volaris logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:40 am
ORD
- CUN
1 stop8h 23m
Volaris
Deal found 7/6![Volaris logo]()
$123
This Mytrip deal was found by Cheapflights users on 7/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/7![Volaris logo]()
$124
This Super.com deal was found by Cheapflights users on 7/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:49 pm
MDW
- CUN
1 stop13h 06m
Volaris
Deal found 7/7![Volaris logo]()
$125
This Booking.com deal was found by Cheapflights users on 7/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:30 am
ORD
- CUN
1 stop15h 35m
Viva
Deal found 7/9![Viva logo]()
$126
This Super.com deal was found by Cheapflights users on 7/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 7/8![Volaris logo]()
$127
This Super.com deal was found by Cheapflights users on 7/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/151:59 am
ORD
- CUN
1 stop12h 07m
Volaris
Deal found 7/8![Volaris logo]()
$127
This Super.com deal was found by Cheapflights users on 7/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:21 am
ORD
- CUN
1 stop11h 53m
Volaris
Deal found 7/11![Volaris logo]()
$128
This Mytrip deal was found by Cheapflights users on 7/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:53 am
ORD
- CUN
1 stop12h 35m
Volaris
Deal found 7/7![Volaris logo]()
$130
This Super.com deal was found by Cheapflights users on 7/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:35 am
ORD
- CUN
1 stop13h 28m
Volaris
Deal found 7/8![Volaris logo]()
$133
This Super.com deal was found by Cheapflights users on 7/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:23 pm
MDW
- CUN
1 stop14h 32m
Volaris
Deal found 7/11![Volaris logo]()
$134
Find flight deals from Chicago to Tulum
Keep the following information in mind while searching for Chicago to Tulum flight deals. Data was last updated July 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Kiwi.com) |
One-way from | $120 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $442 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 12, 2026.
Use the filters below to find and compare flights from Chicago to Tulum that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 8/23
5:10 am-11:50 am
1 stop6h 40m
Cancun
Sun 8/30
2:40 pm-9:10 pm
1 stop6h 30m
$428
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 8/25
6:40 am-6:44 pm
2 stops12h 04m
Cancun
Tue 9/1
6:04 am-2:16 pm
1 stop8h 12m
$437
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 10/19
5:00 am-3:00 pm
1 stop10h 00m
Cancun
Fri 10/23
1:00 pm-10:00 pm
1 stop9h 00m
$447
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 10/10
8:55 am-8:15 pm
2 stops11h 20m
Cancun
Fri 10/16
6:04 am-2:16 pm
1 stop8h 12m
$450
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 10/3
6:35 am-4:05 pm
2 stops9h 30m
Cancun
Wed 10/7
3:20 pm-6:55 pm
Nonstop3h 35m
$454
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 12/3
10:35 am-9:10 pm
1 stop9h 35m
Cancun
Tue 12/8
1:40 pm-10:10 pm
1 stop9h 30m
$456
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 9/23
6:00 am-6:39 pm
2 stops12h 39m
Cancun
Mon 9/28
12:38 pm-11:59 pm
2 stops11h 21m
$456
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 9/23
6:00 am-6:39 pm
2 stops12h 39m
Cancun
Sun 9/27
7:56 am-8:55 pm
2 stops12h 59m
$456
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sat 10/10
9:29 am-8:15 pm
2 stops10h 46m
Cancun
Fri 10/16
8:00 am-6:05 pm
2 stops10h 05m
$460
Quickest round-trip
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Sun 11/15
8:55 am-1:40 pm
Nonstop3h 45m
Cancun
Fri 11/20
2:10 pm-4:50 pm
Nonstop3h 40m
$461
Showing 1-10 of 44 resultsSorted by cheapest first
Best time to book a flight from Chicago to Tulum
Have a flexible travel schedule? Discover the best time to fly to Tulum from Chicago with our price prediction graph.
ORD-CUN
MDW-CUN
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 to Tulum
CHI-TU9
ORD-CUN
MDW-CUN
What is the cheapest time of day to fly from CHI to TU9?
Find hourly flight availability from Chicago 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 12, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 21% on flights from Chicago to Tulum by exploring options for tickets in the afternoon.
Weekly flight availability from Chicago to Tulum
Explore weekly flight availability from Chicago to Tulum. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 12, 2026.
The most flights from CHI to TU9 are scheduled on a Saturday (13 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Chicago 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 July 12, 2026.
Read through reviews of airlines operating flights from Chicago to Tulum, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Tulum. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Tulum
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Complete your trip
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Search flights from Chicago to Tulum by cabin class
Find flights from Chicago to Tulum, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Tulum flights
Browse other Chicago and Tulum flight options. Last updated on July 12, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Tulum flights
Consider these flights traveling from Chicago to Tulum.
Top 10 airlines flying from Chicago to Tulum
Discover the top 10 airlines that operate flights from Chicago 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$115 | Average$406 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$158 | Average$465 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$192 | Average$426 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$560 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$509 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$320 | Average$538 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$360 | Average$429 | FlexibilityNo cancel fee | On-time67% |