Cheapest places to fly from Madison in September
September is the best month to fly almost anywhere: Europe in its second summer at lower fares, the national parks quiet, the beaches warm and cheap, the big US cities back to life. Labor Day weekend is the only peak.
Nonstop from Madison: Chicago (American, United · 1h 05m), Atlanta (Delta · 2h 13m) and Orlando (MX). One stop via Atlanta: Las Vegas; via Dallas: Cancun; via Phoenix: Honolulu. No nonstop seen to Los Angeles and New York on the dates searched recently.
Axel's pick: Chicago, nonstop on American and United and the lowest fare saved for these dates, $293.
Where to fly from Madison in September: the cheapest saved round trips within September to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips, entirely within Sep.
Cheapest right now: Chicago $293 · Atlanta $473 · Las Vegas $512
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | American Airlines | AA4487 + AA1503 | $265.00 | 2026-10-29T01:30:37Z |
| 2026-11-20 · one way | United Airlines | UA3478 + UA2371 | $270.00 | 2026-10-29T01:30:37Z |
| 2026-11-20 · one way | Delta Air Lines | DL3166 + DL648 | $280.00 | 2026-10-29T01:30:37Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA4487 + AA1503 / AA1192 + AA3265 | $566.50 | 2026-10-29T01:30:37Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA3478 + UA2371 / UA2737 + UA1732 | $577.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines / American Airlines | DL3166 + DL648 / AA1192 + AA3265 | $581.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 · one way | American Airlines | AA2480 + AA1778 | $265.00 | 2026-10-29T01:30:37Z |
| 2026-11-20 · one way | Delta Air Lines | DL5518 + DL2016 | $280.00 | 2026-10-29T01:30:37Z |
| 2026-11-20 · one way | Delta Air Lines | DL2681 + DL1939 | $280.00 | 2026-10-29T01:30:37Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA2480 + AA1778 / AA1192 + AA3265 | $566.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA4487 + AA1503 / AA1192 + AA3265 | $566.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA2480 + AA1778 / AA1192 + AA3265 | $566.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA3478 + UA2371 / UA2737 + UA1732 | $577.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines / American Airlines | DL5518 + DL2016 / AA1192 + AA3265 | $581.50 | 2026-10-29T01:30:37Z |
| 2026-11-20 → 2026-11-23 | Delta Air Lines / American Airlines | DL2681 + DL1939 / AA1192 + AA3265 | $581.50 | 2026-10-29T01:30:37Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines / American Airlines | DL3166 + DL648 / AA1192 + AA3265 | $584.50 | 2026-10-29T01:30:37Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines / American Airlines | DL5518 + DL2016 / AA1192 + AA3265 | $584.50 | 2026-10-29T01:30:37Z |
| 2026-11-27 → 2026-12-04 | Delta Air Lines / American Airlines | DL2681 + DL1939 / AA1192 + AA3265 | $584.50 | 2026-10-29T01:30:37Z |
2026-11-20 · one way · $265.00
- American Airlines AA4487 / AA1503: MSN 2026-11-20 05:00:00 → CUN 2026-11-20 13:26:00; 1 stop(s) via ORD; 446 minutes. Local airport times.
- AA4487: MSN 2026-11-20 05:00:00 → ORD 2026-11-20 06:21:00; layover at ORD: 122 minutes.
- AA1503: ORD 2026-11-20 08:23:00 → CUN 2026-11-20 13:26:00.
2026-11-20 · one way · $270.00
- United Airlines UA3478 / UA2371: MSN 2026-11-20 05:00:00 → CUN 2026-11-20 13:43:00; 1 stop(s) via ORD; 463 minutes. Local airport times.
- UA3478: MSN 2026-11-20 05:00:00 → ORD 2026-11-20 06:13:00; layover at ORD: 147 minutes.
- UA2371: ORD 2026-11-20 08:40:00 → CUN 2026-11-20 13:43:00.
2026-11-20 · one way · $280.00
- Delta Air Lines DL3166 / DL648: MSN 2026-11-20 06:32:00 → CUN 2026-11-20 15:30:00; 1 stop(s) via MSP; 478 minutes. Local airport times.
- DL3166: MSN 2026-11-20 06:32:00 → MSP 2026-11-20 07:44:00; layover at MSP: 146 minutes.
- DL648: MSP 2026-11-20 10:10:00 → CUN 2026-11-20 15:30:00.
2026-11-27 → 2026-12-04 · $566.50
- American Airlines AA4487 / AA1503: MSN 2026-11-27 05:00:00 → CUN 2026-11-27 13:26:00; 1 stop(s) via ORD; 446 minutes. Local airport times.
- AA4487: MSN 2026-11-27 05:00:00 → ORD 2026-11-27 06:21:00; layover at ORD: 122 minutes.
- AA1503: ORD 2026-11-27 08:23:00 → CUN 2026-11-27 13:26:00.
- American Airlines AA1192 / AA3265: CUN 2026-12-04 17:13:00 → MSN 2026-12-04 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-12-04 22:30:00 → MSN 2026-12-04 23:49:00.
2026-11-27 → 2026-12-04 · $577.50
- United Airlines UA3478 / UA2371: MSN 2026-11-27 05:00:00 → CUN 2026-11-27 13:43:00; 1 stop(s) via ORD; 463 minutes. Local airport times.
- UA3478: MSN 2026-11-27 05:00:00 → ORD 2026-11-27 06:13:00; layover at ORD: 147 minutes.
- UA2371: ORD 2026-11-27 08:40:00 → CUN 2026-11-27 13:43:00.
- United Airlines UA2737 / UA1732: CUN 2026-12-04 14:55:00 → MSN 2026-12-04 22:23:00; 1 stop(s) via ORD; 508 minutes. Local airport times.
- UA2737: CUN 2026-12-04 14:55:00 → ORD 2026-12-04 17:59:00; layover at ORD: 201 minutes.
- UA1732: ORD 2026-12-04 21:20:00 → MSN 2026-12-04 22:23:00.
2026-11-20 → 2026-11-23 · $581.50
- Delta Air Lines DL3166 / DL648: MSN 2026-11-20 06:32:00 → CUN 2026-11-20 15:30:00; 1 stop(s) via MSP; 478 minutes. Local airport times.
- DL3166: MSN 2026-11-20 06:32:00 → MSP 2026-11-20 07:44:00; layover at MSP: 146 minutes.
- DL648: MSP 2026-11-20 10:10:00 → CUN 2026-11-20 15:30:00.
- American Airlines AA1192 / AA3265: CUN 2026-11-23 17:13:00 → MSN 2026-11-23 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-11-23 22:30:00 → MSN 2026-11-23 23:49:00.
2026-11-20 · one way · $265.00
- American Airlines AA2480 / AA1778: MSN 2026-11-20 06:32:00 → CUN 2026-11-20 16:11:00; 1 stop(s) via CLT; 519 minutes. Local airport times.
- AA2480: MSN 2026-11-20 06:32:00 → CLT 2026-11-20 09:55:00; layover at CLT: 185 minutes.
- AA1778: CLT 2026-11-20 13:00:00 → CUN 2026-11-20 16:11:00.
2026-11-20 · one way · $280.00
- Delta Air Lines DL5518 / DL2016: MSN 2026-11-20 07:00:00 → CUN 2026-11-20 16:10:00; 1 stop(s) via DTW; 490 minutes. Local airport times.
- DL5518: MSN 2026-11-20 07:00:00 → DTW 2026-11-20 09:24:00; layover at DTW: 161 minutes.
- DL2016: DTW 2026-11-20 12:05:00 → CUN 2026-11-20 16:10:00.
2026-11-20 · one way · $280.00
- Delta Air Lines DL2681 / DL1939: MSN 2026-11-20 11:35:00 → CUN 2026-11-20 21:08:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
- DL2681: MSN 2026-11-20 11:35:00 → ATL 2026-11-20 14:35:00; layover at ATL: 234 minutes.
- DL1939: ATL 2026-11-20 18:29:00 → CUN 2026-11-20 21:08:00.
2026-11-27 → 2026-12-04 · $566.50
- American Airlines AA2480 / AA1778: MSN 2026-11-27 06:32:00 → CUN 2026-11-27 16:11:00; 1 stop(s) via CLT; 519 minutes. Local airport times.
- AA2480: MSN 2026-11-27 06:32:00 → CLT 2026-11-27 09:55:00; layover at CLT: 185 minutes.
- AA1778: CLT 2026-11-27 13:00:00 → CUN 2026-11-27 16:11:00.
- American Airlines AA1192 / AA3265: CUN 2026-12-04 17:13:00 → MSN 2026-12-04 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-12-04 22:30:00 → MSN 2026-12-04 23:49:00.
2026-11-20 → 2026-11-23 · $566.50
- American Airlines AA4487 / AA1503: MSN 2026-11-20 05:00:00 → CUN 2026-11-20 13:26:00; 1 stop(s) via ORD; 446 minutes. Local airport times.
- AA4487: MSN 2026-11-20 05:00:00 → ORD 2026-11-20 06:21:00; layover at ORD: 122 minutes.
- AA1503: ORD 2026-11-20 08:23:00 → CUN 2026-11-20 13:26:00.
- American Airlines AA1192 / AA3265: CUN 2026-11-23 17:13:00 → MSN 2026-11-23 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-11-23 22:30:00 → MSN 2026-11-23 23:49:00.
2026-11-20 → 2026-11-23 · $566.50
- American Airlines AA2480 / AA1778: MSN 2026-11-20 06:32:00 → CUN 2026-11-20 16:11:00; 1 stop(s) via CLT; 519 minutes. Local airport times.
- AA2480: MSN 2026-11-20 06:32:00 → CLT 2026-11-20 09:55:00; layover at CLT: 185 minutes.
- AA1778: CLT 2026-11-20 13:00:00 → CUN 2026-11-20 16:11:00.
- American Airlines AA1192 / AA3265: CUN 2026-11-23 17:13:00 → MSN 2026-11-23 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-11-23 22:30:00 → MSN 2026-11-23 23:49:00.
2026-11-20 → 2026-11-23 · $577.50
- United Airlines UA3478 / UA2371: MSN 2026-11-20 05:00:00 → CUN 2026-11-20 13:43:00; 1 stop(s) via ORD; 463 minutes. Local airport times.
- UA3478: MSN 2026-11-20 05:00:00 → ORD 2026-11-20 06:13:00; layover at ORD: 147 minutes.
- UA2371: ORD 2026-11-20 08:40:00 → CUN 2026-11-20 13:43:00.
- United Airlines UA2737 / UA1732: CUN 2026-11-23 14:55:00 → MSN 2026-11-23 22:23:00; 1 stop(s) via ORD; 508 minutes. Local airport times.
- UA2737: CUN 2026-11-23 14:55:00 → ORD 2026-11-23 17:59:00; layover at ORD: 201 minutes.
- UA1732: ORD 2026-11-23 21:20:00 → MSN 2026-11-23 22:23:00.
2026-11-20 → 2026-11-23 · $581.50
- Delta Air Lines DL5518 / DL2016: MSN 2026-11-20 07:00:00 → CUN 2026-11-20 16:10:00; 1 stop(s) via DTW; 490 minutes. Local airport times.
- DL5518: MSN 2026-11-20 07:00:00 → DTW 2026-11-20 09:24:00; layover at DTW: 161 minutes.
- DL2016: DTW 2026-11-20 12:05:00 → CUN 2026-11-20 16:10:00.
- American Airlines AA1192 / AA3265: CUN 2026-11-23 17:13:00 → MSN 2026-11-23 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-11-23 22:30:00 → MSN 2026-11-23 23:49:00.
2026-11-20 → 2026-11-23 · $581.50
- Delta Air Lines DL2681 / DL1939: MSN 2026-11-20 11:35:00 → CUN 2026-11-20 21:08:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
- DL2681: MSN 2026-11-20 11:35:00 → ATL 2026-11-20 14:35:00; layover at ATL: 234 minutes.
- DL1939: ATL 2026-11-20 18:29:00 → CUN 2026-11-20 21:08:00.
- American Airlines AA1192 / AA3265: CUN 2026-11-23 17:13:00 → MSN 2026-11-23 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-11-23 17:13:00 → CLT 2026-11-23 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-11-23 22:30:00 → MSN 2026-11-23 23:49:00.
2026-11-27 → 2026-12-04 · $584.50
- Delta Air Lines DL3166 / DL648: MSN 2026-11-27 06:32:00 → CUN 2026-11-27 15:30:00; 1 stop(s) via MSP; 478 minutes. Local airport times.
- DL3166: MSN 2026-11-27 06:32:00 → MSP 2026-11-27 07:44:00; layover at MSP: 146 minutes.
- DL648: MSP 2026-11-27 10:10:00 → CUN 2026-11-27 15:30:00.
- American Airlines AA1192 / AA3265: CUN 2026-12-04 17:13:00 → MSN 2026-12-04 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-12-04 22:30:00 → MSN 2026-12-04 23:49:00.
2026-11-27 → 2026-12-04 · $584.50
- Delta Air Lines DL5518 / DL2016: MSN 2026-11-27 07:00:00 → CUN 2026-11-27 16:10:00; 1 stop(s) via DTW; 490 minutes. Local airport times.
- DL5518: MSN 2026-11-27 07:00:00 → DTW 2026-11-27 09:24:00; layover at DTW: 161 minutes.
- DL2016: DTW 2026-11-27 12:05:00 → CUN 2026-11-27 16:10:00.
- American Airlines AA1192 / AA3265: CUN 2026-12-04 17:13:00 → MSN 2026-12-04 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-12-04 22:30:00 → MSN 2026-12-04 23:49:00.
2026-11-27 → 2026-12-04 · $584.50
- Delta Air Lines DL2681 / DL1939: MSN 2026-11-27 11:35:00 → CUN 2026-11-27 21:08:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
- DL2681: MSN 2026-11-27 11:35:00 → ATL 2026-11-27 14:35:00; layover at ATL: 234 minutes.
- DL1939: ATL 2026-11-27 18:29:00 → CUN 2026-11-27 21:08:00.
- American Airlines AA1192 / AA3265: CUN 2026-12-04 17:13:00 → MSN 2026-12-04 23:49:00; 1 stop(s) via CLT; 456 minutes. Local airport times.
- AA1192: CUN 2026-12-04 17:13:00 → CLT 2026-12-04 20:14:00; layover at CLT: 136 minutes.
- AA3265: CLT 2026-12-04 22:30:00 → MSN 2026-12-04 23:49:00.
More dates for this route
More trip ideas from Madison
- Bachelorette and bachelor party trips from Madison, priced for 6
- Big event trips from Madison: Super Bowl, Coachella, Kentucky Derby and more
- College football bowl and playoff trips from Madison
- Family vacations from Madison, priced for 4
- Flights to your cruise port from Madison
- Fourth of July trips from Madison
- Gay & LGBTQ+ friendly cities to visit from Madison
- Graduation trips from Madison
- Halloween trips from Madison: Salem, New Orleans, Horror Nights, Derry and Transylvania
- Labor Day weekend trips from Madison
- MLK weekend getaways from Madison
- New Year's Eve trips from Madison
- Presidents' Day weekend getaways from Madison
- Spring break trips from Madison
- Thanksgiving trips from Madison
- The best US cities to visit from Madison
- Theme park trips from Madison, priced for 4
- Veterans Day weekend trips from Madison
- Winter break trips from Madison
- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · for 4 days · for a week · for two weeks
Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Madison
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Chicago (ORD) | Chicago's architecture, lakefront and deep-dish | Nonstop · American, United · 1h 05m | $293 (airline $309) | Sep 3–6, 2027 | Check prices |
| Atlanta (ATL) | Atlanta's museums, food and the civil rights trail | Nonstop · Delta · 2h 13m | $473 (airline $499) | Sep 11–18, 2027 | Check prices |
| Las Vegas (LAS) | Las Vegas' Strip, shows and day trips to the canyons | 1 stop via Atlanta | $512 (airline $539) | Sep 3–6, 2027 | Check prices |
| Cancun (CUN) | Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby | 1 stop via Dallas | $578 (airline $610) | Sep 11–18, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki, Diamond Head and Pearl Harbor on Oahu | 1 stop via Phoenix | $705 (airline $746) | Sep 11–18, 2027 | Check prices |
| Orlando (MCO) | Orlando's theme parks | Nonstop · MX | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
| Los Angeles (LAX) | Los Angeles' beaches, Hollywood and museums | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
| New York (JFK) | New York's museums, Broadway and neighborhoods | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
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
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
Hotels with an Axel review in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Hacienda Cancun · Akuazul Resorts Adults Only · All 148 reviewed hotels in Cancun
For AI assistants
- This page: Cheapest places to fly from Madison in September. Where to fly from Madison in September: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within September, nonstop options first, and a link to search your own dates.
- 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.