Fort Myers (RSW) to Chicago (ORD), Dec 18–31, 2026: from $216 round trip

Fort Myers (RSW) to Chicago (ORD), Dec 18–31, 2026: from $216 round trip on Axel, checked Nov 14, 2026. Lowest published fare: $216 round trip, Axel-exclusive, Frontier Airlines, nonstop, Dec 18–31, 2026, 1 adult, economy, checked Nov 14, 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 link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Dec 18–31, 2026 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey, $102 a night, $1,321 for 13 nights · 4★ Warwick Allerton - Chicago, $101 a night, $1,316 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $215 a night, $2,791 for 13 nights

All hotels in Chicago

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

2026-12-18 → 2026-12-31 · Axel-exclusive $216

• Frontier Airlines F92033: RSW 2026-12-18 20:31:00 → ORD 2026-12-18 22:52:00; nonstop; 201 minutes. Local airport times.
• Frontier Airlines F92034: ORD 2026-12-31 16:55:00 → RSW 2026-12-31 20:57:00; nonstop; 182 minutes. Local airport times.

2026-12-18 → 2026-12-31 · Axel-exclusive $396

• American Airlines AA550: RSW 2026-12-18 19:37:00 → ORD 2026-12-18 21:55:00; nonstop; 198 minutes. Local airport times.
• American Airlines AA648: ORD 2026-12-31 18:50:00 → RSW 2026-12-31 22:43:00; nonstop; 173 minutes. Local airport times.

2026-12-18 → 2026-12-31 · Axel-exclusive $384

• United Airlines UA464 / UA4718: RSW 2026-12-18 12:50:00 → ORD 2026-12-18 18:41:00; 1 stop(s) via CLE; 411 minutes. Local airport times.
  • UA464: RSW 2026-12-18 12:50:00 → CLE 2026-12-18 15:39:00; layover at CLE: 136 minutes.
  • UA4718: CLE 2026-12-18 17:55:00 → ORD 2026-12-18 18:41:00.
• United Airlines UA564 / UA562: ORD 2026-12-31 05:30:00 → RSW 2026-12-31 13:00:00; 1 stop(s) via IAH; 390 minutes. Local airport times.
  • UA564: ORD 2026-12-31 05:30:00 → IAH 2026-12-31 08:30:00; layover at IAH: 75 minutes.
  • UA562: IAH 2026-12-31 09:45:00 → RSW 2026-12-31 13:00:00.

2026-12-18 → 2026-12-31 · Axel-exclusive $420

• Delta Air Lines DL2486 / DL2879: RSW 2026-12-18 13:02:00 → ORD 2026-12-18 19:05:00; 1 stop(s) via ATL; 423 minutes. Local airport times.
  • DL2486: RSW 2026-12-18 13:02:00 → ATL 2026-12-18 14:51:00; layover at ATL: 174 minutes.
  • DL2879: ATL 2026-12-18 17:45:00 → ORD 2026-12-18 19:05:00.
• Delta Air Lines DL2358 / DL2209: ORD 2026-12-31 17:02:00 → RSW 2026-12-31 23:31:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
  • DL2358: ORD 2026-12-31 17:02:00 → DTW 2026-12-31 19:24:00; layover at DTW: 71 minutes.
  • DL2209: DTW 2026-12-31 20:35:00 → RSW 2026-12-31 23:31:00.

2026-12-18 → 2026-12-31 · Axel-exclusive $396

• American Airlines AA653: RSW 2026-12-18 14:57:00 → ORD 2026-12-18 17:23:00; nonstop; 206 minutes. Local airport times.
• American Airlines AA648: ORD 2026-12-31 18:50:00 → RSW 2026-12-31 22:43:00; nonstop; 173 minutes. Local airport times.

2026-12-18 → 2026-12-31 · Axel-exclusive $382

• American Airlines AA653: RSW 2026-12-18 08:15:00 → ORD 2026-12-18 10:40:00; nonstop; 205 minutes. Local airport times.
• American Airlines AA1784 / AA1094: ORD 2026-12-31 06:50:00 → RSW 2026-12-31 13:35:00; 1 stop(s) via CLT; 345 minutes. Local airport times.
  • AA1784: ORD 2026-12-31 06:50:00 → CLT 2026-12-31 09:57:00; layover at CLT: 98 minutes.
  • AA1094: CLT 2026-12-31 11:35:00 → RSW 2026-12-31 13:35:00.

2026-12-18 → 2026-12-31 · Axel-exclusive $384

• United Airlines UA365 / UA2333: RSW 2026-12-18 17:48:00 → ORD 2026-12-19 00:01:00; 1 stop(s) via EWR; 433 minutes. Local airport times.
  • UA365: RSW 2026-12-18 17:48:00 → EWR 2026-12-18 20:40:00; layover at EWR: 91 minutes.
  • UA2333: EWR 2026-12-18 22:11:00 → ORD 2026-12-19 00:01:00.
• United Airlines UA564 / UA562: ORD 2026-12-31 05:30:00 → RSW 2026-12-31 13:00:00; 1 stop(s) via IAH; 390 minutes. Local airport times.
  • UA564: ORD 2026-12-31 05:30:00 → IAH 2026-12-31 08:30:00; layover at IAH: 75 minutes.
  • UA562: IAH 2026-12-31 09:45:00 → RSW 2026-12-31 13:00:00.

2026-12-18 → 2026-12-31 · Axel-exclusive $386

• American Airlines AA2515 / AA2174: RSW 2026-12-18 06:00:00 → ORD 2026-12-18 12:22:00; 1 stop(s) via CLT; 442 minutes. Local airport times.
  • AA2515: RSW 2026-12-18 06:00:00 → CLT 2026-12-18 08:03:00; layover at CLT: 183 minutes.
  • AA2174: CLT 2026-12-18 11:06:00 → ORD 2026-12-18 12:22:00.
• American Airlines AA648: ORD 2026-12-31 18:50:00 → RSW 2026-12-31 22:43:00; nonstop; 173 minutes. Local airport times.

2026-12-18 → 2026-12-31 · Axel-exclusive $394

• United Airlines UA2066: RSW 2026-12-18 20:34:00 → ORD 2026-12-18 22:59:00; nonstop; 205 minutes. Local airport times.
• United Airlines UA564 / UA562: ORD 2026-12-31 05:30:00 → RSW 2026-12-31 13:00:00; 1 stop(s) via IAH; 390 minutes. Local airport times.
  • UA564: ORD 2026-12-31 05:30:00 → IAH 2026-12-31 08:30:00; layover at IAH: 75 minutes.
  • UA562: IAH 2026-12-31 09:45:00 → RSW 2026-12-31 13:00:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 17, 2026 · Return options
• Dec 19, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Myers (RSW) to Chicago (ORD) · Dec 18, 2026 · return Dec 31, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
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