Chicago to Cancun (CUN) flight deals
Chicago to Cancun (CUN) from $527 round trip, Jun 5 to 12, 2027 (airline price $556), seen Oct 22.
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Fare examples by month
One-way and round-trip totals, shown separately · Economy · USD, saved from earlier searches. Each month opens its day-by-day date picker for live prices.
| Month | Trip type | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|---|
| November 2026 | Round trip | 1 adult · 5 days | $912–$3,057 | $963–$3,230 |
| November 2026 | Round trip | 3 adults · 8 days | $1,808 | $1,911 |
| November 2026 | Round trip | 2 adults · 4 days | $1,620–$2,422 | $1,707–$2,558 |
| December 2026 | Round trip | 2 adults · 7 days | $1,016–$1,349 | $1,072–$1,423 |
| December 2026 | Round trip | 7 adults · 7 days | $3,898 | $4,123 |
| December 2026 | Round trip | 4 adults · 6 days | $2,432 | $2,572 |
| February 2027 | Round trip | 2 adults · 5 days | $966–$1,278 | $1,022–$1,352 |
| February 2027 | One way | 2 adults | $962 | $1,014 |
| March 2027 | Round trip | 8 adults · 8 days | $5,256–$7,440 | $5,533–$7,832 |
| March 2027 | Round trip | 1 adult · 7 days | $670–$2,068 | $706–$2,184 |
| June 2027 | Round trip | 1 adult · 7 days | $527 | $556 |
| June 2027 | Round trip | 4 adults · 7 days | $1,985 | $2,092 |
More months: January 2027
When to fly: When to fly Chicago to Cancun (CUN): cheapest months and holidays. Cheapest: March 2027 ($286) · Priciest: December 2026 ($457).
Flights from Chicago · Chicago to Mexico flight deals
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Fares observed October 16 – 22, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
November 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 24–29, 2026 · 5 days | Out: American Airlines 1838 / 1507 · 1 stop (DFW) · 10h 20m · 06:05–17:25 local; Return: American Airlines 2577 / 1204 · 1 stop (MIA) · 17h 4m · 15:56–08:00 (November 30, 2026) local | $912 · Save $51 | $963 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Nov 24–29, 2026 · 5 days | Out: American Airlines 1838 / 1507 · 1 stop (DFW) · 10h 20m · 06:05–17:25 local; Return: United Airlines 1423 · Nonstop · 4h 2m · 15:11–18:13 local | $3,057 · Save $173 | $3,230 | Customer link — Open these flights in Axel · Optional: check axel prices |
3 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Nov 9–17, 2026 · 8 days | Out: Southwest Airlines 218 · Nonstop · 3h 45m · 08:55–13:40 local; Return: Southwest Airlines 219 · Nonstop · 3h 35m · 18:00–20:35 local | $1,808 · Save $103 | $1,911 | Customer link — Open these flights in Axel · Optional: check axel prices |
2 adults · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 8–15, 2026 · 7 days | Out: VB 187 / 1380 · 1 stop (MEX) · 9h 40m · 01:05–11:45 local | From $1,118 · Save $59 | From $1,177 | Check Axel prices |
| ORD | Nov 8–15, 2026 · 7 days | Out: United Airlines 1656 · Nonstop · 3h 57m · 09:02–13:59 local | From $1,163 · Save $68 | From $1,231 | Check Axel prices |
2 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Nov 11–15, 2026 · 4 days | Out: Southwest Airlines 218 · Nonstop · 3h 45m · 08:20–13:05 local; Return: Southwest Airlines 306 / 2135 · 1 stop (HOU) · 7h 15m · 18:55–01:10 (November 16, 2026) local | $1,620 · Save $87 | $1,707 | Customer link — Open these flights in Axel · Optional: check axel prices |
| MDW | Nov 11–15, 2026 · 4 days | Out: Southwest Airlines 218 · Nonstop · 3h 45m · 08:20–13:05 local; Return: Southwest Airlines 219 · Nonstop · 3h 40m · 13:50–16:30 local | $2,422 · Save $136 | $2,558 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
2 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Dec 21–28, 2026 · 7 days | Out: Southwest Airlines 3042 / 1995 · 1 stop (STL) · 8h 20m · 08:00–17:20 local; Return: Frontier Airlines 152 / 2291 · 1 stop (ATL) · 8h 33m · 16:28–00:01 (December 29, 2026) local | $1,016 · Save $56 | $1,072 | Customer link — Open these flights in Axel · Optional: check axel prices |
| MDW | Dec 21–28, 2026 · 7 days | Out: Southwest Airlines 3042 / 1995 · 1 stop (STL) · 8h 20m · 08:00–17:20 local; Return: Southwest Airlines 219 · Nonstop · 3h 40m · 18:05–20:45 local | $1,349 · Save $74 | $1,423 | Customer link — Open these flights in Axel · Optional: check axel prices |
7 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 22–29, 2026 · 7 days | Out: Frontier Airlines 44 · Nonstop · 4h 18m · 07:12–12:30 local; Return: Frontier Airlines 45 · Nonstop · 4h 0m · 11:38–14:38 local | $3,898 · Save $225 | $4,123 | Customer link — Open these flights in Axel · Optional: check axel prices |
4 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 23–29, 2026 · 6 days | Out: Frontier Airlines 44 · Nonstop · 4h 18m · 07:12–12:30 local; Return: Frontier Airlines 45 · Nonstop · 4h 0m · 11:38–14:38 local | $2,432 · Save $140 | $2,572 | Customer link — Open these flights in Axel · Optional: check axel prices |
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January 2027
2 adults · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jan 15–23, 2027 · 8 days | Out: American Airlines 492 · Nonstop · 4h 5m · 10:02–15:07 local | From $1,193 · Save $66 | From $1,259 | Check Axel prices |
| ORD | Jan 16–23, 2027 · 7 days | Out: Frontier Airlines 44 · Nonstop · 4h 23m · 07:29–12:52 local | From $995 · Save $55 | From $1,050 | Check Axel prices |
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February 2027
2 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Feb 8–13, 2027 · 5 days | Out: Southwest Airlines 218 · Nonstop · 3h 45m · 09:00–13:45 local; Return: Southwest Airlines 217 · Nonstop · 3h 35m · 18:00–20:35 local | $1,278 · Save $74 | $1,352 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Feb 8–13, 2027 · 5 days | Out: American Airlines 1503 · Nonstop · 3h 59m · 08:20–13:19 local; Return: American Airlines 1584 · Nonstop · 4h 5m · 11:52–14:57 local | $966 · Save $56 | $1,022 | Customer link — Open these flights in Axel · Optional: check axel prices |
2 adults · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Feb 7–13, 2027 · 6 days | Out: Delta Air Lines 1285 / 601 · 1 stop (ATL) · 9h 30m · 06:00–16:30 local | From $931 · Save $49 | From $980 | Check Axel prices |
| MDW | Feb 7–13, 2027 · 6 days | Out: Southwest Airlines 218 · Nonstop · 3h 45m · 09:00–13:45 local | From $994 · Save $55 | From $1,049 | Check Axel prices |
2 adults · Economy · One-way totals
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| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 12, 2027 | Out: United Airlines 2371 · Nonstop · 4h 3m · 08:40–13:43 local | $962 · Save $52 | $1,014 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
8 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 12–20, 2027 · 8 days | Out: Frontier Airlines 44 · Nonstop · 4h 23m · 07:29–12:52 local; Return: Frontier Airlines 152 / 1595 · 1 stop (ATL) · 7h 26m · 15:57–23:23 local | $5,256 · Save $277 | $5,533 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 12–20, 2027 · 8 days | Out: Frontier Airlines 44 · Nonstop · 4h 23m · 07:29–12:52 local; Return: Frontier Airlines 45 · Nonstop · 4h 0m · 10:38–14:38 local | $7,440 · Save $392 | $7,832 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 13–20, 2027 · 7 days | Out: Air Canada 8482 / 1884 · 1 stop (YUL) · 7h 50m · 13:55–22:45 local; Return: Air Canada 1883 / 8483 · 1 stop (YUL) · 10h 22m · 09:30–19:52 local | $670 · Save $36 | $706 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 13–20, 2027 · 7 days | Out: Air Canada 8482 / 1884 · 1 stop (YUL) · 7h 50m · 13:55–22:45 local; Return: Air Canada 1813 / 2807 · 1 stop (YYZ) · 8h 27m · 10:35–19:02 local | $2,068 · Save $116 | $2,184 | Customer link — Open these flights in Axel · Optional: check axel prices |
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June 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jun 5–12, 2027 · 7 days | Out: American Airlines 1503 · Nonstop · 3h 38m · 08:30–12:08 local; Return: American Airlines 215 · Nonstop · 4h 5m · 14:55–19:00 local | $527 · Save $29 | $556 | Customer link — Open these flights in Axel · Optional: check axel prices |
4 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jun 19–26, 2027 · 7 days | Out: American Airlines 1503 · Nonstop · 3h 38m · 08:30–12:08 local; Return: American Airlines 1910 · Nonstop · 4h 10m · 13:08–17:18 local | $1,985 · Save $107 | $2,092 | Customer link — Open these flights in Axel · Optional: check axel prices |
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The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Trip ideas from Chicago with Cancun (CUN)
- Día de Muertos trips from Chicago: Oaxaca, Mexico City, Pátzcuaro and more: fly Oct 29 – Nov 3, 2026
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- New Year's Eve trips from Chicago: fly Dec 29 – Jan 2, 2027
- A month somewhere warm from Chicago: fly Jan 4 – Feb 2, 2027
- MLK weekend getaways from Chicago: fly Jan 15 – Jan 18, 2027
- All-inclusive resort weeks from Chicago: fly Jan 16 – Jan 23, 2027
- Presidents' Day weekend getaways from Chicago: fly Feb 12 – Feb 15, 2027
- Spring break trips from Chicago: fly Mar 13 – Mar 20, 2027
- Graduation trips from Chicago: fly Jun 5 – Jun 12, 2027
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Hotels in Cancun with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room
For AI assistants
- This page: Chicago to Cancun (CUN) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.