Fort Myers (RSW) to Chicago (ORD) · Dec 7, 2026 · return Dec 21, 2026

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Dec 7–21, 2026 · 14 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,546 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,844 total · 5★ Nobu Hotel Chicago, $5,207 total

All hotels in Chicago

Route overview: Fort Myers to Chicago (ORD) flight deals

2026-12-07 → 2026-12-21 · Axel-exclusive $216.00

• Frontier Airlines F92033: RSW 2026-12-07 20:31:00 → ORD 2026-12-07 22:49:00; nonstop; 198 minutes. Local airport times.
• Frontier Airlines F92034: ORD 2026-12-21 15:30:00 → RSW 2026-12-21 19:32:00; nonstop; 182 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $396.00

• American Airlines AA3289: RSW 2026-12-07 11:49:00 → ORD 2026-12-07 14:16:00; nonstop; 207 minutes. Local airport times.
• American Airlines AA3289: ORD 2026-12-21 06:59:00 → RSW 2026-12-21 10:57:00; nonstop; 178 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $408.00

• United Airlines UA2420: RSW 2026-12-07 18:15:00 → ORD 2026-12-07 20:34:00; nonstop; 199 minutes. Local airport times.
• United Airlines UA1504: ORD 2026-12-21 18:08:00 → RSW 2026-12-21 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $350.50

• XP XP356 / XP421: RSW 2026-12-07 12:15:00 → ORD 2026-12-07 18:18:00; 1 stop(s) via HVN; 423 minutes. Local airport times.
  • XP356: RSW 2026-12-07 12:15:00 → HVN 2026-12-07 15:15:00; layover at HVN: 70 minutes.
  • XP421: HVN 2026-12-07 16:25:00 → ORD 2026-12-07 18:18:00.
• United Airlines UA1504: ORD 2026-12-21 18:08:00 → RSW 2026-12-21 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $420.00

• Delta Air Lines DL2277 / DL1716: RSW 2026-12-07 08:00:00 → ORD 2026-12-07 13:59:00; 1 stop(s) via DTW; 419 minutes. Local airport times.
  • DL2277: RSW 2026-12-07 08:00:00 → DTW 2026-12-07 10:54:00; layover at DTW: 153 minutes.
  • DL1716: DTW 2026-12-07 13:27:00 → ORD 2026-12-07 13:59:00.
• Delta Air Lines DL2358 / DL2209: ORD 2026-12-21 17:02:00 → RSW 2026-12-21 23:31:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
  • DL2358: ORD 2026-12-21 17:02:00 → DTW 2026-12-21 19:24:00; layover at DTW: 71 minutes.
  • DL2209: DTW 2026-12-21 20:35:00 → RSW 2026-12-21 23:31:00.

2026-12-07 → 2026-12-21 · Axel-exclusive $396.00

• American Airlines AA669: RSW 2026-12-07 19:40:00 → ORD 2026-12-07 22:00:00; nonstop; 200 minutes. Local airport times.
• American Airlines AA3289: ORD 2026-12-21 06:59:00 → RSW 2026-12-21 10:57:00; nonstop; 178 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $408.00

• United Airlines UA1284: RSW 2026-12-07 16:41:00 → ORD 2026-12-07 19:00:00; nonstop; 199 minutes. Local airport times.
• United Airlines UA1504: ORD 2026-12-21 18:08:00 → RSW 2026-12-21 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $386.00

• American Airlines AA2515 / AA2174: RSW 2026-12-07 06:00:00 → ORD 2026-12-07 12:22:00; 1 stop(s) via CLT; 442 minutes. Local airport times.
  • AA2515: RSW 2026-12-07 06:00:00 → CLT 2026-12-07 08:03:00; layover at CLT: 183 minutes.
  • AA2174: CLT 2026-12-07 11:06:00 → ORD 2026-12-07 12:22:00.
• American Airlines AA3289: ORD 2026-12-21 06:59:00 → RSW 2026-12-21 10:57:00; nonstop; 178 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $398.00

• United Airlines UA464 / UA4718: RSW 2026-12-07 12:50:00 → ORD 2026-12-07 18:41:00; 1 stop(s) via CLE; 411 minutes. Local airport times.
  • UA464: RSW 2026-12-07 12:50:00 → CLE 2026-12-07 15:39:00; layover at CLE: 136 minutes.
  • UA4718: CLE 2026-12-07 17:55:00 → ORD 2026-12-07 18:41:00.
• United Airlines UA1504: ORD 2026-12-21 18:08:00 → RSW 2026-12-21 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $398.00

• United Airlines UA365 / UA2333: RSW 2026-12-07 17:48:00 → ORD 2026-12-08 00:01:00; 1 stop(s) via EWR; 433 minutes. Local airport times.
  • UA365: RSW 2026-12-07 17:48:00 → EWR 2026-12-07 20:40:00; layover at EWR: 91 minutes.
  • UA2333: EWR 2026-12-07 22:11:00 → ORD 2026-12-08 00:01:00.
• United Airlines UA1504: ORD 2026-12-21 18:08:00 → RSW 2026-12-21 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-07 → 2026-12-21 · Axel-exclusive $420.00

• Delta Air Lines DL2486 / DL2879: RSW 2026-12-07 13:02:00 → ORD 2026-12-07 19:05:00; 1 stop(s) via ATL; 423 minutes. Local airport times.
  • DL2486: RSW 2026-12-07 13:02:00 → ATL 2026-12-07 14:51:00; layover at ATL: 174 minutes.
  • DL2879: ATL 2026-12-07 17:45:00 → ORD 2026-12-07 19:05:00.
• Delta Air Lines DL2358 / DL2209: ORD 2026-12-21 17:02:00 → RSW 2026-12-21 23:31:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
  • DL2358: ORD 2026-12-21 17:02:00 → DTW 2026-12-21 19:24:00; layover at DTW: 71 minutes.
  • DL2209: DTW 2026-12-21 20:35:00 → RSW 2026-12-21 23:31:00.

Explore this route

• All dates for this route
• Dec 6, 2026 · Return options
• Dec 8, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Myers (RSW) to Chicago (ORD) · Dec 7, 2026 · return Dec 21, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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