Boston (BOS) to Chicago (MDW), Jan 4–16, 2027: from $248 round trip

Boston (BOS) to Chicago (MDW), Jan 4–16, 2027: from $248 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $248 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Jan 4–16, 2027, 1 adult, economy, checked Nov 13, 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 (Jan 4–16, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $934 for 12 nights · 4★ Freehand Chicago, $73 a night, $878 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $2,743 for 12 nights

All hotels in Chicago

Route overview: Boston to Chicago (MDW) flight deals

2027-01-04 → 2027-01-16 · Axel-exclusive $304

• Southwest Airlines WN816: BOS 2027-01-04 17:55:00 → MDW 2027-01-04 19:40:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN4113: MDW 2027-01-16 07:40:00 → BOS 2027-01-16 10:55:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-16 · Axel-exclusive $248

• Frontier Airlines F93511 / F92779: BOS 2027-01-04 12:15:00 → MDW 2027-01-04 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-04 12:15:00 → ATL 2027-01-04 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-04 16:45:00 → MDW 2027-01-04 17:47:00.
• Southwest Airlines WN4113: MDW 2027-01-16 07:40:00 → BOS 2027-01-16 10:55:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-16 · Axel-exclusive $394

• Delta Air Lines DL2222 / DL4677: BOS 2027-01-04 13:04:00 → MDW 2027-01-04 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-04 13:04:00 → DTW 2027-01-04 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-04 17:40:00 → MDW 2027-01-04 18:01:00.
• Delta Air Lines DL5469 / DL2558: MDW 2027-01-16 10:24:00 → BOS 2027-01-16 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-16 10:24:00 → MSP 2027-01-16 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-16 13:09:00 → BOS 2027-01-16 17:01:00.

2027-01-04 → 2027-01-16 · Axel-exclusive $304

• Southwest Airlines WN816: BOS 2027-01-04 18:30:00 → MDW 2027-01-04 20:15:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2902: MDW 2027-01-16 18:55:00 → BOS 2027-01-16 22:15:00; nonstop; 140 minutes. Local airport times.

2027-01-04 → 2027-01-16 · Axel-exclusive $316

• Southwest Airlines WN4765 / WN651: BOS 2027-01-04 14:25:00 → MDW 2027-01-04 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
  • WN4765: BOS 2027-01-04 14:25:00 → BNA 2027-01-04 16:15:00; layover at BNA: 195 minutes.
  • WN651: BNA 2027-01-04 19:30:00 → MDW 2027-01-04 21:05:00.
• Southwest Airlines WN4113: MDW 2027-01-16 07:40:00 → BOS 2027-01-16 10:55:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-16 · Axel-exclusive $316

• Southwest Airlines WN819 / WN287: BOS 2027-01-04 05:35:00 → MDW 2027-01-04 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-04 05:35:00 → STL 2027-01-04 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-04 10:55:00 → MDW 2027-01-04 12:05:00.
• Southwest Airlines WN4113: MDW 2027-01-16 07:40:00 → BOS 2027-01-16 10:55:00; nonstop; 135 minutes. Local airport times.

2027-01-04 → 2027-01-16 · Axel-exclusive $316

• Southwest Airlines WN1426 / WN1070: BOS 2027-01-04 07:25:00 → MDW 2027-01-04 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN1426: BOS 2027-01-04 07:25:00 → BWI 2027-01-04 09:15:00; layover at BWI: 110 minutes.
  • WN1070: BWI 2027-01-04 11:05:00 → MDW 2027-01-04 12:15:00.
• Southwest Airlines WN4113: MDW 2027-01-16 07:40:00 → BOS 2027-01-16 10:55:00; nonstop; 135 minutes. Local airport times.

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
• Jan 3, 2027 · Return options
• Jan 5, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (MDW) · Jan 4, 2027 · return Jan 16, 2027: 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.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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• 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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