Prices may change. Select and confirm the full itinerary with the booking provider. Dates can differ between airport cards.
A great Cancun trip starts with a fare worth finding. Compare the latest samples below, then join our upcoming free newsletter to get standout Chicago flight finds in your inbox.
Same airports & dates. Each provider checks its own current prices.
ORD → CUN · Feb 18–Feb 25
Search fare; select your return flight to confirm.
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$292 for Feb 18–Feb 25, 2027, compared with $676 for Dec 28–Jan 4, 2027.
12 seven-night date pairs from ORD to the same arrival-airport set (CUN). Lowest returned fare per date pair; checks within 24 hours. Airlines, stops and ticket conditions can differ. A travel-date comparison, not a booking-time prediction.
Explore the cheaper date samples ↗The same dated search ranged from $254 to $359 across 61 historical price observations.
ORD → CUN · Feb 18–Feb 25, 2027. Google Flights history covers Jul 29, 2026–Sep 27, 2026. The percentage is the low below the high. This does not prove when you should book or what subscribers will save.
See the price history ↗ORD → CUN · Feb 18–Feb 25, 2027. Recorded Sep 27, 2026.
Our archive starts Sep 27, 2026 and contains 236 seven-night fare observations for this route. Search fare; return may require confirmation. This is our record, not an industry-wide all-time low or a current offer.
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Same dates: Feb 18–Feb 25. Same arrival airports: CUN.
1 stop outbound
1 stop outbound
$158 separates the lowest and highest airport sample for these dates. These are search-result fares for seven-night trips. Flight times, stops and baggage can differ. Ground transport is excluded.
Across 12 matched date pairs in this sample, ORD had the lowest airport fare 12 time(s); MDW had the lowest airport fare 0 time(s). Ties count for each airport. This describes the sampled dates only.
A cheaper ticket can come with a pricier ride. Add your own round-trip transport estimate to the matched fares.
Flight sample $568
$568fare + transportFlight sample $1,253
$1,253fare + transportAdd your transport estimates to compare your total.
One adult, economy, USD. The two fares use identical dates and arrival-airport sets, checked within 24 hours. Transport starts at $0 because we don’t know your starting point. Baggage and other extras are excluded. Prices and itineraries can differ.
MDW → CUN, Apr 10. Nonstop.
Across 24 seven-night airport/date searches. Includes connecting carriers.
Lowest: $292, Feb 18–Feb 25 from ORD.
MDW, ORD in these outbound results. This is not a full schedule.
Derived from the current seven-night observations on this page. Outbound times describe the outbound journey only; fare amounts are round-trip search results. See sources and coverage.
Lowest fare in each sampled departure month. Seven-night trips only.
Swipe to see more months →
Tap a bar to see the dates, airports and check time behind that sample.
| Departure month | Lowest sample | Date pairs |
|---|---|---|
| 2026-10 | $568 | 1 |
| 2026-11 | $312 | 1 |
| 2026-12 | $302 | 2 |
| 2027-01 | $302 | 1 |
| 2027-02 | $292 | 1 |
| 2027-03 | $312 | 1 |
| 2027-04 | $523 | 1 |
| 2027-05 | $504 | 1 |
| 2027-06 | $473 | 2 |
| 2027-07 | $518 | 1 |
Sampled dates, not a complete fare calendar. Each month can have different date coverage. This chart describes future travel dates, not past price movements.
Prices checked within seven days. Use the filters to find a trip that fits.
| Dates / airports | Airline / outbound | Round trip | Check price |
|---|---|---|---|
| Feb 18–Feb 25ORD → CUN · 7 nights |  Viva1 stop · 19h 20m | $292Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → CUN · 7 nights | Viva1 stop · 9h 25m | $302Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → CUN · 7 nights | Viva1 stop · 9h 20m | $302Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13ORD → CUN · 7 nights | Viva1 stop · 20h 30m | $312Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Mar 15–Mar 22ORD → CUN · 7 nights | Viva1 stop · 9h 30m | $312Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → CUN · 7 nights |  FrontierNonstop · 4h 23m | $388Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13ORD → CUN · 7 nights |  American1 stop · 12h 24m | $440Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25ORD → CUN · 7 nights | American1 stop · 12h 20m | $440Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Mar 15–Mar 22ORD → CUN · 7 nights | American1 stop · 7h 8m | $440Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → CUN · 7 nights |  JetBlue1 stop · 8h 15m | $442Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → CUN · 7 nights | American1 stop · 6h 13m | $445Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → CUN · 7 nights | AmericanNonstop · 4h 5m | $446Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25ORD → CUN · 7 nights | FrontierNonstop · 4h 23m | $449Return also checkedChecked Sep 27 | Google Skyscanner ↗ItineraryORD → CUN CUN → ORD |
| Jan 23–Jan 30MDW → CUN · 7 nights |  Delta1 stop · 9h 40m | $450Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25MDW → CUN · 7 nights | Delta1 stop · 15h 35m | $450Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Mar 15–Mar 22ORD → CUN · 7 nights | AmericanNonstop · 4h 3m | $454Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13ORD → CUN · 7 nights |  UnitedNonstop · 4h 3m | $455Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → CUN · 7 nights | FrontierNonstop · 3h 56m | $459Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9MDW → CUN · 7 nights |  Southwest1 stop · 7h 10m | $469Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8ORD → CUN · 7 nights | AmericanNonstop · 3h 45m | $473Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13MDW → CUN · 7 nights | Frontier1 stop · 6h 25m | $500Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| May 6–May 13ORD → CUN · 7 nights | AmericanNonstop · 3h 52m | $504Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jul 23–Jul 30ORD → CUN · 7 nights | AmericanNonstop · 3h 51m | $518Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Apr 10–Apr 17ORD → CUN · 7 nights | Delta1 stop · 16h 10m | $523Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| May 6–May 13MDW → CUN · 7 nights | SouthwestNonstop · 3h 35m | $543Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 11–Oct 18ORD → CUN · 7 nights | Viva1 stop · 10h 15m | $568Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Apr 10–Apr 17MDW → CUN · 7 nights | Delta1 stop · 16h 1m | $575Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8MDW → CUN · 7 nights | SouthwestNonstop · 3h 35m | $593Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 27–Jul 4ORD → CUN · 7 nights | AmericanNonstop · 3h 45m | $626Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25MDW → CUN · 7 nights | SouthwestNonstop · 3h 45m | $647Return also checkedChecked Sep 27 | Google Skyscanner ↗ItineraryMDW → CUN CUN → MDW |
| Mar 15–Mar 22MDW → CUN · 7 nights | Southwest2 stops · 12h 35m | $649Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 28–Jan 4ORD → CUN · 7 nights | Frontier1 stop · 24h 21m | $676Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jul 23–Jul 30MDW → CUN · 7 nights | Delta2 stops · 14h 56m | $759Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 28–Jan 4MDW → CUN · 7 nights | Southwest2 stops · 12h 15m | $777Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 27–Jul 4MDW → CUN · 7 nights | Delta2 stops · 14h 56m | $1,176Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 11–Oct 18MDW → CUN · 7 nights | Frontier1 stop · 6h 17m | $1,253Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
No samples match these filters. Try another airport or trip length.
Prices can change. Cabin baggage and checked bags are not assumed included. Confirm the complete itinerary, airline fare rules and final price on the booking site.
ORD → CUN · Feb 18–Feb 25, 2027
| Observation date | Price |
|---|---|
| Jul 29, 2026 | $294 |
| Jul 30, 2026 | $294 |
| Jul 31, 2026 | $299 |
| Aug 1, 2026 | $305 |
| Aug 2, 2026 | $305 |
| Aug 3, 2026 | $305 |
| Aug 4, 2026 | $305 |
| Aug 5, 2026 | $305 |
| Aug 6, 2026 | $305 |
| Aug 7, 2026 | $305 |
| Aug 8, 2026 | $305 |
| Aug 9, 2026 | $305 |
| Aug 10, 2026 | $311 |
| Aug 11, 2026 | $312 |
| Aug 12, 2026 | $323 |
| Aug 13, 2026 | $323 |
| Aug 14, 2026 | $323 |
| Aug 15, 2026 | $323 |
| Aug 16, 2026 | $340 |
| Aug 17, 2026 | $343 |
| Aug 18, 2026 | $332 |
| Aug 19, 2026 | $337 |
| Aug 20, 2026 | $353 |
| Aug 21, 2026 | $354 |
| Aug 22, 2026 | $354 |
| Aug 23, 2026 | $354 |
| Aug 24, 2026 | $354 |
| Aug 25, 2026 | $359 |
| Aug 26, 2026 | $359 |
| Aug 27, 2026 | $354 |
| Aug 28, 2026 | $354 |
| Aug 29, 2026 | $353 |
| Aug 30, 2026 | $353 |
| Aug 31, 2026 | $353 |
| Sep 1, 2026 | $353 |
| Sep 2, 2026 | $353 |
| Sep 3, 2026 | $353 |
| Sep 4, 2026 | $353 |
| Sep 5, 2026 | $353 |
| Sep 6, 2026 | $353 |
| Sep 7, 2026 | $353 |
| Sep 8, 2026 | $353 |
| Sep 9, 2026 | $353 |
| Sep 10, 2026 | $273 |
| Sep 11, 2026 | $273 |
| Sep 12, 2026 | $288 |
| Sep 13, 2026 | $303 |
| Sep 14, 2026 | $302 |
| Sep 15, 2026 | $302 |
| Sep 16, 2026 | $254 |
| Sep 17, 2026 | $255 |
| Sep 18, 2026 | $254 |
| Sep 19, 2026 | $302 |
| Sep 20, 2026 | $302 |
| Sep 21, 2026 | $302 |
| Sep 22, 2026 | $294 |
| Sep 23, 2026 | $293 |
| Sep 24, 2026 | $292 |
| Sep 25, 2026 | $292 |
| Sep 26, 2026 | $292 |
| Sep 27, 2026 | $292 |
Google Flights price history returned through Scrapingdog for the dates and settings above. It is not a destination-wide average or a prediction. Source checked Sep 27, 2026.
Airport context and source-backed details to help you compare the whole journey.
Cancún, Mexico · Airport coordinates 21.041, -86.873
Lowest sample to CUN: $292 round trip from ORD, Feb 18–Feb 25. Different arrival airports may use different dates.
Airport informationThis page searches CUN — Cancún International Airport. Airport coverage follows the destination city market in the passenger dataset, with minor airports excluded. Always check the airport code on both legs: a city search can include different arrival airports, and the cheapest option may not be closest to where you are staying.
Read the sourceBTS recorded 466,977 scheduled passengers departing O’Hare and Midway for this destination city market from 2025-07 to 2026-06. That puts it at number 31 in our selected ranking. These are historical on-flight market passengers, not unique travelers, current flight frequencies or a measure of search popularity.
Read the sourceThe airport reference places Cancún International Airport in Cancún, Mexico, at 21.041°, -86.873°. Use the airport’s official information to plan your arrival and return journey. Our fare table compares air travel only; ground transfers, luggage and accommodation can change the total trip budget.
Read the sourceKeep an eye on the whole travel budget, from your first night to your last mile.
Compare places to stay in Cancun. Add your dates, check the location, and compare the final total and cancellation terms.
Explore Cancun stays ↗Booking.com · choose your travel datesPlanning a drive beyond Cancun? Compare rental cars, mileage, deposits and pickup hours. City-only trip? Public transit may suit you better.
Compare rental cars ↗Discover Cars · enter CUN and your datesThese are planning links, not priced offers. Hotel and car availability is checked by the provider. We currently receive no commission from these links.
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The lowest seven-night round-trip search fare in our archive is $292, recorded Sep 27, 2026 for ORD to CUN, Feb 18–Feb 25, 2027. Our route archive starts Sep 27, 2026. This is our observed record, not an industry-wide all-time low, a verified booking price or a current offer.
Our lowest current seven-night sample is $292 round trip for one adult in economy, from ORD to CUN, Feb 18–Feb 25, 2027. It was checked Sep 27, 2026. This is a dated search result, not a guaranteed ticket price; confirm the return and full fare conditions before paying.
For the matched Feb 18–Feb 25, 2027 search, ORD had the lowest sample at $292. The highest and lowest airport fares were $158 apart. That applies to those dates and settings only. Try other matched dates and add your own ground transport cost in the airport calculator above.
The current sample includes a nonstop outbound from ORD to CUN on Jan 23, 2027, with a round-trip search fare of $388. Check the return direction separately: a nonstop outbound does not guarantee a nonstop return.
The travel-period chart compares only the dates we sampled. It cannot establish the cheapest month of the year. Start with a promising sampled period, then check nearby dates with the same trip length. The separate history chart tracks one specific search over time; it is not a travel calendar.
This destination market includes Cancún International Airport (CUN). Check the exact arrival code on the fare you choose, then compare the onward journey to your accommodation. The arrival section links airport information and our source-backed planning notes.
Not necessarily. The buttons open separate searches with matching airports and dates when a dated sample is available. Providers can show different airlines, sellers, baggage rules and live prices. The sampled Google Flights price is never a Skyscanner quote.
Do not assume bags are included unless the provider explicitly confirms them. Our research shows flight search fares; the accommodation and rental-car links are separate planning tools. Compare the final total, cancellation terms and location before booking any part of the trip.
Answers use the dated research and sources on this page. Read our flight-saving field notes for a broader planning checklist.
Get our best flight finds in your inbox ↗This page contains 234 current search-result observations across 24 airport/date searches. Route research is compiled by the Chicago Flight Research desk from the sources below.
Destination photography: photographer, source and reuse license. Airline logos identify the carriers shown in results; no partnership is implied.
BTS demand period: 2025-07 to 2026-06. Searches use one adult, economy, USD and the US market. We do not sell tickets, guarantee fares, or infer baggage inclusions. Read the full methodology
