Chicago to Mexico flight deals
Compare flights from Chicago to Mexico across upcoming months. Explore the dated fares below, or search your own trip.
Browse months: November 2026 · December 2026
Compare destinations for the same trip
Nov 10–17, 2026 · 1 adult · Economy · Round trip
- ORD → Puerto Vallarta (PVR): $306 Axel vs $323 airline · Save $17. Check PVR prices
- MDW → Cancun (CUN): $425 Axel vs $450 airline · Save $25. Check CUN prices
- MDW → Mexico City (MEX): $433 Axel vs $457 airline · Save $24. Check MEX prices
- MDW → Los Cabos (SJD): $548 Axel vs $579 airline · Save $31. Check SJD prices
- MDW → Puerto Vallarta (PVR): $592 Axel vs $626 airline · Save $34. Check PVR prices
- ORD → Los Cabos (SJD): $736 Axel vs $778 airline · Save $42. Check SJD prices
Explore destinations
Cancun (CUN) · Mexico City (MEX) · Puerto Vallarta (PVR) · Los Cabos (SJD)
Compare destinations
Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Cancun (CUN) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 50m / 9h 3m | $425 · Save $25 | $450 | Check Axel prices |
| MDW | Cancun (CUN) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 50m / 7h 48m | $502 · Save $26 | $528 | Check Axel prices |
| MDW | Mexico City (MEX) | Nov 10–17, 2026 · 7 days | 1 stop / 2 stops · 7h 20m / 12h 9m | $433 · Save $24 | $457 | Check Axel prices |
| MDW | Mexico City (MEX) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 7h 38m | $683 · Save $38 | $721 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Nov 10–17, 2026 · 7 days | 1 stop / 2 stops · 6h 5m / 14h 0m | $592 · Save $34 | $626 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 5m / 8h 30m | $683 · Save $38 | $721 | Check Axel prices |
| ORD | Puerto Vallarta (PVR) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 10h 21m / 6h 43m | $306 · Save $17 | $323 | Check Axel prices |
| ORD | Los Cabos (SJD) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 16h 45m / 24h 19m | $736 · Save $42 | $778 | Check Axel prices |
| MDW | Los Cabos (SJD) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 7h 25m | $548 · Save $31 | $579 | Check Axel prices |
| MDW | Cancun (CUN) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 5h 50m / 8h 0m | $425 · Save $25 | $450 | Check Axel prices |
| MDW | Cancun (CUN) | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 5h 50m / 3h 40m | $566 · Save $31 | $597 | Check Axel prices |
| MDW | Mexico City (MEX) | Nov 17–24, 2026 · 7 days | 2 stops / 2 stops · 10h 35m / 19h 18m | $487 · Save $28 | $515 | Check Axel prices |
| MDW | Mexico City (MEX) | Nov 17–24, 2026 · 7 days | 2 stops / 1 stop · 10h 35m / 7h 38m | $820 · Save $47 | $867 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Nov 17–24, 2026 · 7 days | 1 stop / 2 stops · 7h 45m / 16h 2m | $569 · Save $32 | $601 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 45m / 7h 59m | $683 · Save $38 | $721 | Check Axel prices |
| ORD | Puerto Vallarta (PVR) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 10h 21m / 6h 43m | $306 · Save $17 | $323 | Check Axel prices |
| ORD | Los Cabos (SJD) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 13h 54m / 24h 19m | $736 · Save $42 | $778 | Check Axel prices |
| MDW | Los Cabos (SJD) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 9h 15m | $548 · Save $31 | $579 | Check Axel prices |
| MDW | Los Cabos (SJD) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 6h 55m | $581 · Save $33 | $614 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Cancun (CUN) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 6m / 9h 1m | $422 · Save $23 | $445 | Check Axel prices |
| MDW | Cancun (CUN) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 6m / 7h 44m | $425 · Save $25 | $450 | Check Axel prices |
| MDW | Mexico City (MEX) | Dec 1–8, 2026 · 7 days | 2 stops / 1 stop · 23h 3m / 7h 36m | $436 · Save $25 | $461 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 6h 5m / 8h 25m | $602 · Save $35 | $637 | Check Axel prices |
| ORD | Puerto Vallarta (PVR) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 8h 11m / 6h 56m | $373 · Save $22 | $395 | Check Axel prices |
| MDW | Los Cabos (SJD) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 8h 5m / 7h 20m | $548 · Save $31 | $579 | Check Axel prices |
| ORD | Los Cabos (SJD) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 8h 0m / 24h 19m | $819 · Save $47 | $866 | Check Axel prices |
| MDW | Cancun (CUN) | Dec 8–15, 2026 · 7 days | Nonstop / 1 stop · 3h 45m / 7h 20m | $422 · Save $24 | $446 | Check Axel prices |
| MDW | Cancun (CUN) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 3h 45m / 3h 35m | $504 · Save $28 | $532 | Check Axel prices |
| MDW | Mexico City (MEX) | Dec 8–15, 2026 · 7 days | 2 stops / 1 stop · 10h 35m / 10h 24m | $429 · Save $23 | $452 | Check Axel prices |
| MDW | Mexico City (MEX) | Dec 8–15, 2026 · 7 days | 2 stops / 1 stop · 10h 35m / 7h 36m | $513 · Save $27 | $540 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Dec 8–15, 2026 · 7 days | 1 stop / 2 stops · 6h 5m / 14h 0m | $569 · Save $32 | $601 | Check Axel prices |
| MDW | Puerto Vallarta (PVR) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 6h 5m / 8h 25m | $589 · Save $33 | $622 | Check Axel prices |
| ORD | Puerto Vallarta (PVR) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 23h 0m / 19h 18m | $474 · Save $27 | $501 | Check Axel prices |
| ORD | Puerto Vallarta (PVR) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 23h 0m / 18h 4m | $484 · Save $27 | $511 | Check Axel prices |
| MDW | Los Cabos (SJD) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 9h 5m | $548 · Save $31 | $579 | Check Axel prices |
| MDW | Los Cabos (SJD) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 7h 20m | $568 · Save $32 | $600 | Check Axel prices |
| ORD | Los Cabos (SJD) | Dec 8–15, 2026 · 7 days | 1 stop / Nonstop · 8h 7m / 4h 33m | $518 · Save $30 | $548 | Check Axel prices |
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.
Keep exploring
For AI assistants
- This page: Chicago to Mexico flight deals. Chicago to Mexico flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Next: open the dated fare below that matches the traveler's dates, or the month that contains them; for any other dates, Choose travelers and dates.
- Every link here is complete and ready to open. Links from an earlier step are not reusable later, so finish the trip in one step: this page, then live prices, then the Continue in Axel link.
- If a link can no longer be opened: search for "Axel Chicago to Mexico flight deals" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-to-mexico; an address the traveler opens always works.
- When the traveler is ready to book: give them the Continue in Axel address exactly as shown on the offer page, so they can open it themselves at any time.