Boston (BOS) to Chicago (MDW) · Dec 31, 2026 · return Jan 11, 2027

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 31 – Jan 11, 2027 · 11 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,238 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,422 total · 5★ Nobu Hotel Chicago, $4,086 total

All hotels in Chicago

Route overview: Boston to Chicago (MDW) flight deals

2026-12-31 → 2027-01-11 · Axel-exclusive $303.75

• Southwest Airlines WN816: BOS 2026-12-31 18:30:00 → MDW 2026-12-31 20:15:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN4113: MDW 2027-01-11 07:40:00 → BOS 2027-01-11 10:55:00; nonstop; 135 minutes. Local airport times.

2026-12-31 → 2027-01-11 · Axel-exclusive $247.50

• Frontier Airlines F93511 / F92779: BOS 2026-12-31 12:15:00 → MDW 2026-12-31 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2026-12-31 12:15:00 → ATL 2026-12-31 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2026-12-31 16:45:00 → MDW 2026-12-31 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-11 13:00:00 → BOS 2027-01-11 16:10:00; nonstop; 130 minutes. Local airport times.

2026-12-31 → 2027-01-11 · Axel-exclusive $393.75

• Delta Air Lines DL2222 / DL4677: BOS 2026-12-31 13:04:00 → MDW 2026-12-31 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-12-31 13:04:00 → DTW 2026-12-31 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-12-31 17:40:00 → MDW 2026-12-31 18:01:00.
• Delta Air Lines DL5469 / DL2558: MDW 2027-01-11 10:24:00 → BOS 2027-01-11 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-11 10:24:00 → MSP 2027-01-11 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-11 13:09:00 → BOS 2027-01-11 17:01:00.

2026-12-31 → 2027-01-11 · Axel-exclusive $303.75

• Southwest Airlines WN816: BOS 2026-12-31 17:55:00 → MDW 2026-12-31 19:40:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2900: MDW 2027-01-11 13:00:00 → BOS 2027-01-11 16:10:00; nonstop; 130 minutes. Local airport times.

2026-12-31 → 2027-01-11 · Axel-exclusive $316.25

• Southwest Airlines WN819 / WN287: BOS 2026-12-31 05:35:00 → MDW 2026-12-31 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2026-12-31 05:35:00 → STL 2026-12-31 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2026-12-31 10:55:00 → MDW 2026-12-31 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-11 13:00:00 → BOS 2027-01-11 16:10:00; nonstop; 130 minutes. Local airport times.

2026-12-31 → 2027-01-11 · Axel-exclusive $316.25

• Southwest Airlines WN4765 / WN651: BOS 2026-12-31 14:25:00 → MDW 2026-12-31 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
  • WN4765: BOS 2026-12-31 14:25:00 → BNA 2026-12-31 16:15:00; layover at BNA: 195 minutes.
  • WN651: BNA 2026-12-31 19:30:00 → MDW 2026-12-31 21:05:00.
• Southwest Airlines WN2900: MDW 2027-01-11 13:00:00 → BOS 2027-01-11 16:10:00; nonstop; 130 minutes. Local airport times.

2026-12-31 → 2027-01-11 · Axel-exclusive $316.25

• Southwest Airlines WN1426 / WN1070: BOS 2026-12-31 07:25:00 → MDW 2026-12-31 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN1426: BOS 2026-12-31 07:25:00 → BWI 2026-12-31 09:15:00; layover at BWI: 110 minutes.
  • WN1070: BWI 2026-12-31 11:05:00 → MDW 2026-12-31 12:15:00.
• Southwest Airlines WN2900: MDW 2027-01-11 13:00:00 → BOS 2027-01-11 16:10:00; nonstop; 130 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (MDW) · Dec 31, 2026 · return Jan 11, 2027: 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.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• 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 Boston 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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