Jacksonville (JAX) to Chicago (MDW), Jan 25, 2027: round trips from $176, one way from $95

Jacksonville (JAX) to Chicago (MDW), Jan 25, 2027: round trips from $176, one way from $95 on Axel, checked Oct 29, 2026. Lowest published fares: $176 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 25–26, 2027; $95 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 25, 2027; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

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 lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 25–26, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $126 total · 5★ Waldorf Astoria Chicago, $413 total
• Hotels in Chicago for these nights (Jan 25–27, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $252 total · 5★ Waldorf Astoria Chicago, $818 total
• Hotels in Chicago for these nights (Jan 25–28, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $233 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $378 total · 5★ Waldorf Astoria Chicago, $1,231 total
• Hotels in Chicago for these nights (Jan 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $308 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $523 total · 5★ Nobu Hotel Chicago, $1,620 total
• Hotels in Chicago for these nights (Jan 25–30, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $392 total · 4★ Millennium Hotel Knickerbocker Chicago, $653 total · 5★ Nobu Hotel Chicago, $2,007 total
• Hotels in Chicago for these nights (Jan 25–31, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $467 total · 4★ Millennium Hotel Knickerbocker Chicago, $776 total · 5★ Nobu Hotel Chicago, $2,383 total
• Hotels in Chicago for these nights (Jan 25 – Feb 1, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $550 total · 4★ Millennium Hotel Knickerbocker Chicago, $891 total · 5★ Nobu Hotel Chicago, $2,732 total
• Hotels in Chicago for these nights (Jan 25 – Feb 2, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $639 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,007 total · 5★ Nobu Hotel Chicago, $3,110 total
• Hotels in Chicago for these nights (Jan 25 – Feb 3, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $728 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,122 total · 5★ Nobu Hotel Chicago, $3,523 total
• Hotels in Chicago for these nights (Jan 25 – Feb 4, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $817 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,235 total · 5★ Nobu Hotel Chicago, $3,914 total
• Hotels in Chicago for these nights (Jan 25 – Feb 5, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $916 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,346 total · 5★ Nobu Hotel Chicago, $4,296 total
• Hotels in Chicago for these nights (Jan 25 – Feb 6, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,005 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,476 total · 5★ Nobu Hotel Chicago, $4,687 total
• Hotels in Chicago for these nights (Jan 25 – Feb 7, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,094 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,608 total · 5★ Nobu Hotel Chicago, $5,078 total
• Hotels in Chicago for these nights (Jan 25 – Feb 8, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,193 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,723 total · 5★ Nobu Hotel Chicago, $5,427 total

All hotels in Chicago

Route overview: Jacksonville to Chicago (MDW) flight deals

2027-01-25 · one way · Axel-exclusive $95.00

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.

2027-01-25 · one way · Axel-exclusive $147.25

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.

2027-01-25 → 2027-01-26 · Axel-exclusive $175.76

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-26 13:11:00 → JAX 2027-01-26 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-26 13:11:00 → ATL 2027-01-26 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-26 18:09:00 → JAX 2027-01-26 19:25:00.

2027-01-25 → 2027-01-26 · Axel-exclusive $275.50

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-01-26 19:00:00 → JAX 2027-01-26 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-01-27 · Axel-exclusive $175.76

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-27 13:11:00 → JAX 2027-01-27 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-27 13:11:00 → ATL 2027-01-27 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-27 18:09:00 → JAX 2027-01-27 19:25:00.

2027-01-25 → 2027-01-27 · Axel-exclusive $275.50

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-01-27 19:00:00 → JAX 2027-01-27 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-01-28 · Axel-exclusive $175.76

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-28 13:11:00 → JAX 2027-01-28 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-28 13:11:00 → ATL 2027-01-28 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-28 18:09:00 → JAX 2027-01-28 19:25:00.

2027-01-25 → 2027-01-28 · Axel-exclusive $275.50

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2041: MDW 2027-01-28 12:50:00 → JAX 2027-01-28 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-01-29 · Axel-exclusive $175.76

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-29 13:11:00 → JAX 2027-01-29 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-29 13:11:00 → ATL 2027-01-29 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-29 18:09:00 → JAX 2027-01-29 19:25:00.

2027-01-25 → 2027-01-29 · Axel-exclusive $275.50

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2262: MDW 2027-01-29 08:00:00 → JAX 2027-01-29 11:25:00; nonstop; 145 minutes. Local airport times.

2027-01-25 → 2027-01-31 · Axel-exclusive $175.76

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-31 13:11:00 → JAX 2027-01-31 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-31 13:11:00 → ATL 2027-01-31 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-31 18:09:00 → JAX 2027-01-31 19:25:00.

2027-01-25 → 2027-01-31 · Axel-exclusive $268.38

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN3092 / WN4807: MDW 2027-01-31 13:40:00 → JAX 2027-01-31 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-01-31 13:40:00 → STL 2027-01-31 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-01-31 18:15:00 → JAX 2027-01-31 21:15:00.

2027-01-25 → 2027-02-01 · Axel-exclusive $180.38

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-02-01 13:11:00 → JAX 2027-02-01 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-02-01 13:11:00 → ATL 2027-02-01 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-02-01 18:09:00 → JAX 2027-02-01 19:25:00.

2027-01-25 → 2027-02-01 · Axel-exclusive $282.75

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-02-01 19:00:00 → JAX 2027-02-01 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $180.38

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-02-02 13:11:00 → JAX 2027-02-02 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-02-02 13:11:00 → ATL 2027-02-02 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-02-02 18:09:00 → JAX 2027-02-02 19:25:00.

2027-01-25 → 2027-02-02 · Axel-exclusive $282.75

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-02-02 19:00:00 → JAX 2027-02-02 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-02-04 · Axel-exclusive $180.38

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-02-04 13:11:00 → JAX 2027-02-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-02-04 13:11:00 → ATL 2027-02-04 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-02-04 18:09:00 → JAX 2027-02-04 19:25:00.

2027-01-25 → 2027-02-04 · Axel-exclusive $282.75

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-02-05 · Axel-exclusive $180.38

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-02-05 13:11:00 → JAX 2027-02-05 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-02-05 13:11:00 → ATL 2027-02-05 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-02-05 18:09:00 → JAX 2027-02-05 19:25:00.

2027-01-25 → 2027-02-05 · Axel-exclusive $282.75

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times.

2027-01-25 → 2027-02-06 · Axel-exclusive $180.38

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-02-06 13:11:00 → JAX 2027-02-06 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-02-06 13:11:00 → ATL 2027-02-06 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-02-06 18:09:00 → JAX 2027-02-06 19:25:00.

2027-01-25 → 2027-02-06 · Axel-exclusive $282.75

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-02-06 19:00:00 → JAX 2027-02-06 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-25 → 2027-02-08 · Axel-exclusive $180.38

• Frontier Airlines F91549 / F92291: JAX 2027-01-25 19:03:00 → MDW 2027-01-25 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-25 19:03:00 → ATL 2027-01-25 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-25 22:48:00 → MDW 2027-01-25 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-02-08 13:11:00 → JAX 2027-02-08 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-02-08 13:11:00 → ATL 2027-02-08 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-02-08 18:09:00 → JAX 2027-02-08 19:25:00.

2027-01-25 → 2027-02-08 · Axel-exclusive $282.75

• Southwest Airlines WN2264: JAX 2027-01-25 18:55:00 → MDW 2027-01-25 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-02-08 19:00:00 → JAX 2027-02-08 22:15:00; nonstop; 135 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 24, 2027 · Return options
• Jan 26, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Jacksonville (JAX) to Chicago (MDW) · Jan 25, 2027 · choose your return date: 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 link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Jacksonville to Chicago (MDW) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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