Fort Myers (RSW) to Chicago (ORD), Dec 19–28, 2026: from $252 round trip

Fort Myers (RSW) to Chicago (ORD), Dec 19–28, 2026: from $252 round trip on Axel, checked Nov 12, 2026. Lowest published fare: $252 round trip, Axel-exclusive, Frontier Airlines, nonstop, Dec 19–28, 2026, 1 adult, economy, checked Nov 12, 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 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $101 a night, $911 for 9 nights · 4★ Freehand Chicago, $72 a night, $646 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $219 a night, $1,969 for 9 nights

All hotels in Chicago

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

2026-12-19 → 2026-12-28 · Axel-exclusive $252

• Frontier Airlines F92033: RSW 2026-12-19 21:57:00 → ORD 2026-12-20 00:18:00; nonstop; 201 minutes. Local airport times.
• Frontier Airlines F92034: ORD 2026-12-28 15:30:00 → RSW 2026-12-28 19:32:00; nonstop; 182 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $462

• American Airlines AA653: RSW 2026-12-19 08:15:00 → ORD 2026-12-19 10:40:00; nonstop; 205 minutes. Local airport times.
• American Airlines AA3289: ORD 2026-12-28 06:59:00 → RSW 2026-12-28 10:57:00; nonstop; 178 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $476

• United Airlines UA2462: RSW 2026-12-19 14:35:00 → ORD 2026-12-19 17:00:00; nonstop; 205 minutes. Local airport times.
• United Airlines UA1504: ORD 2026-12-28 18:08:00 → RSW 2026-12-28 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $396

• XP XP356 / XP421: RSW 2026-12-19 12:15:00 → ORD 2026-12-19 18:18:00; 1 stop(s) via HVN; 423 minutes. Local airport times.
  • XP356: RSW 2026-12-19 12:15:00 → HVN 2026-12-19 15:15:00; layover at HVN: 70 minutes.
  • XP421: HVN 2026-12-19 16:25:00 → ORD 2026-12-19 18:18:00.
• United Airlines UA1504: ORD 2026-12-28 18:08:00 → RSW 2026-12-28 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $490

• Delta Air Lines DL2277 / DL1716: RSW 2026-12-19 08:00:00 → ORD 2026-12-19 13:59:00; 1 stop(s) via DTW; 419 minutes. Local airport times.
  • DL2277: RSW 2026-12-19 08:00:00 → DTW 2026-12-19 10:54:00; layover at DTW: 153 minutes.
  • DL1716: DTW 2026-12-19 13:27:00 → ORD 2026-12-19 13:59:00.
• Delta Air Lines DL2358 / DL2209: ORD 2026-12-28 17:02:00 → RSW 2026-12-28 23:31:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
  • DL2358: ORD 2026-12-28 17:02:00 → DTW 2026-12-28 19:24:00; layover at DTW: 71 minutes.
  • DL2209: DTW 2026-12-28 20:35:00 → RSW 2026-12-28 23:31:00.

2026-12-19 → 2026-12-28 · Axel-exclusive $462

• American Airlines AA653: RSW 2026-12-19 14:57:00 → ORD 2026-12-19 17:23:00; nonstop; 206 minutes. Local airport times.
• American Airlines AA648: ORD 2026-12-28 20:22:00 → RSW 2026-12-29 00:29:00; nonstop; 187 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $476

• United Airlines UA2347: RSW 2026-12-19 09:05:00 → ORD 2026-12-19 11:24:00; nonstop; 199 minutes. Local airport times.
• United Airlines UA1504: ORD 2026-12-28 18:08:00 → RSW 2026-12-28 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $448

• American Airlines AA2515 / AA2174: RSW 2026-12-19 06:00:00 → ORD 2026-12-19 12:22:00; 1 stop(s) via CLT; 442 minutes. Local airport times.
  • AA2515: RSW 2026-12-19 06:00:00 → CLT 2026-12-19 08:03:00; layover at CLT: 183 minutes.
  • AA2174: CLT 2026-12-19 11:06:00 → ORD 2026-12-19 12:22:00.
• American Airlines AA3289: ORD 2026-12-28 06:59:00 → RSW 2026-12-28 10:57:00; nonstop; 178 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $462

• United Airlines UA365 / UA2333: RSW 2026-12-19 17:48:00 → ORD 2026-12-20 00:01:00; 1 stop(s) via EWR; 433 minutes. Local airport times.
  • UA365: RSW 2026-12-19 17:48:00 → EWR 2026-12-19 20:40:00; layover at EWR: 91 minutes.
  • UA2333: EWR 2026-12-19 22:11:00 → ORD 2026-12-20 00:01:00.
• United Airlines UA1504: ORD 2026-12-28 18:08:00 → RSW 2026-12-28 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $462

• United Airlines UA464 / UA4718: RSW 2026-12-19 12:50:00 → ORD 2026-12-19 18:41:00; 1 stop(s) via CLE; 411 minutes. Local airport times.
  • UA464: RSW 2026-12-19 12:50:00 → CLE 2026-12-19 15:39:00; layover at CLE: 136 minutes.
  • UA4718: CLE 2026-12-19 17:55:00 → ORD 2026-12-19 18:41:00.
• United Airlines UA1504: ORD 2026-12-28 18:08:00 → RSW 2026-12-28 22:15:00; nonstop; 187 minutes. Local airport times.

2026-12-19 → 2026-12-28 · Axel-exclusive $490

• Delta Air Lines DL2486 / DL2879: RSW 2026-12-19 13:02:00 → ORD 2026-12-19 19:05:00; 1 stop(s) via ATL; 423 minutes. Local airport times.
  • DL2486: RSW 2026-12-19 13:02:00 → ATL 2026-12-19 14:51:00; layover at ATL: 174 minutes.
  • DL2879: ATL 2026-12-19 17:45:00 → ORD 2026-12-19 19:05:00.
• Delta Air Lines DL2358 / DL2209: ORD 2026-12-28 17:02:00 → RSW 2026-12-28 23:31:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
  • DL2358: ORD 2026-12-28 17:02:00 → DTW 2026-12-28 19:24:00; layover at DTW: 71 minutes.
  • DL2209: DTW 2026-12-28 20:35:00 → RSW 2026-12-28 23:31:00.

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 18, 2026 · Return options
• Dec 20, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Myers (RSW) to Chicago (ORD) · Dec 19, 2026 · return Dec 28, 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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