Chicago (MDW) to Cancun (CUN), Jan 15, 2027: round trips from $410, one way from $210

Chicago (MDW) to Cancun (CUN), Jan 15, 2027: round trips from $410, one way from $210 on Axel, checked Oct 29, 2026. Lowest published fares: $410 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 15–16, 2027; $210 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 15, 2027; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Exact travel dates Airline Flights Times, duration, stops Total price Price issued (UTC)
2027-01-15 · one way Southwest Airlines WN1123 + WN1609 08:50:00→17:55:00 8h 05m 1 stop via BWI Axel-exclusive $210.00 2026-10-29T01:29:05Z
2027-01-15 · one way Delta Air Lines DL2417 + DL1939 13:02:00→21:08:00 7h 06m 1 stop via ATL Axel-exclusive $245.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-16 Southwest Airlines WN1123 + WN1609 / WN217 08:50:00→17:55:00 8h 05m 1 stop via BWI · 17:15:00→19:50:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-16 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-17 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 08:20:00→10:50:00 3h 30m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-17 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-18 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:00:00→20:35:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-18 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-19 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:05:00→20:45:00 3h 40m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-19 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-20 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:05:00→20:40:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-20 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-21 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:00:00→20:35:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-21 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-22 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:00:00→20:35:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-22 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-23 Southwest Airlines WN1123 + WN1609 / WN217 08:50:00→17:55:00 8h 05m 1 stop via BWI · 17:15:00→19:50:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-23 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-24 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 08:20:00→10:50:00 3h 30m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-24 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-25 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:00:00→20:35:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-25 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-26 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:05:00→20:45:00 3h 40m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-26 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-27 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:05:00→20:40:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-27 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-28 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:00:00→20:35:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-28 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-29 Southwest Airlines WN1123 + WN1609 / WN219 08:50:00→17:55:00 8h 05m 1 stop via BWI · 18:00:00→20:35:00 3h 35m nonstop Axel-exclusive $410.00 2026-10-29T01:29:05Z
2027-01-15 → 2027-01-29 Delta Air Lines DL2417 + DL1939 / DL1962 + DL1076 13:02:00→21:08:00 7h 06m 1 stop via ATL · 16:20:00→22:22:00 7h 02m 1 stop via ATL Axel-exclusive $445.00 2026-10-29T01:29:05Z

Hotels in Cancun for these trips

Hotels: under a trip, hotels in Cancun for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Cancun

Route overview: Chicago to Cancun (CUN) flight deals

2027-01-15 · one way · Axel-exclusive $210.00

2027-01-15 · one way · Axel-exclusive $245.00

2027-01-15 → 2027-01-16 · Axel-exclusive $410.00

2027-01-15 → 2027-01-16 · Axel-exclusive $445.00

2027-01-15 → 2027-01-17 · Axel-exclusive $410.00

2027-01-15 → 2027-01-17 · Axel-exclusive $445.00

2027-01-15 → 2027-01-18 · Axel-exclusive $410.00

2027-01-15 → 2027-01-18 · Axel-exclusive $445.00

2027-01-15 → 2027-01-19 · Axel-exclusive $410.00

2027-01-15 → 2027-01-19 · Axel-exclusive $445.00

2027-01-15 → 2027-01-21 · Axel-exclusive $410.00

2027-01-15 → 2027-01-21 · Axel-exclusive $445.00

2027-01-15 → 2027-01-22 · Axel-exclusive $410.00

2027-01-15 → 2027-01-22 · Axel-exclusive $445.00

2027-01-15 → 2027-01-23 · Axel-exclusive $410.00

2027-01-15 → 2027-01-23 · Axel-exclusive $445.00

2027-01-15 → 2027-01-25 · Axel-exclusive $410.00

2027-01-15 → 2027-01-25 · Axel-exclusive $445.00

2027-01-15 → 2027-01-26 · Axel-exclusive $410.00

2027-01-15 → 2027-01-26 · Axel-exclusive $445.00

2027-01-15 → 2027-01-27 · Axel-exclusive $410.00

2027-01-15 → 2027-01-27 · Axel-exclusive $445.00

2027-01-15 → 2027-01-29 · Axel-exclusive $410.00

2027-01-15 → 2027-01-29 · Axel-exclusive $445.00

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