Chicago (MDW) to Boston (BOS), Jan 18, 2027: round trips from $283, one way from $155

Chicago (MDW) to Boston (BOS), Jan 18, 2027: round trips from $283, one way from $155 on Axel, checked Oct 29, 2026. Lowest published fares: $283 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 18–20, 2027; $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 18, 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 Boston for these trips

Hotels: under a trip, hotels in Boston 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 Boston for these nights (Jan 18–19, 2027 · 1 night · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–20, 2027 · 2 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–21, 2027 · 3 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–22, 2027 · 4 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–23, 2027 · 5 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–24, 2027 · 6 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–25, 2027 · 7 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–26, 2027 · 8 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–27, 2027 · 9 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–28, 2027 · 10 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–29, 2027 · 11 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–30, 2027 · 12 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18–31, 2027 · 13 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel
• Hotels in Boston for these nights (Jan 18 – Feb 1, 2027 · 14 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2027-01-18 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.

2027-01-18 · one way · Axel-exclusive $205.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.

2027-01-18 → 2027-01-19 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-19 17:55:00 → MDW 2027-01-19 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-19 · Axel-exclusive $390.00

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

2027-01-18 → 2027-01-20 · Axel-exclusive $282.50

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN819 / WN287: BOS 2027-01-20 05:35:00 → MDW 2027-01-20 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-20 05:35:00 → STL 2027-01-20 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-20 10:55:00 → MDW 2027-01-20 12:05:00.

2027-01-18 → 2027-01-20 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-20 13:04:00 → MDW 2027-01-20 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-20 13:04:00 → DTW 2027-01-20 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-20 17:40:00 → MDW 2027-01-20 18:01:00.

2027-01-18 → 2027-01-21 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-21 17:55:00 → MDW 2027-01-21 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-21 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-21 13:04:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-21 13:04:00 → DTW 2027-01-21 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.

2027-01-18 → 2027-01-22 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-22 18:30:00 → MDW 2027-01-22 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-22 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-22 13:04:00 → MDW 2027-01-22 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-22 13:04:00 → DTW 2027-01-22 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-22 17:40:00 → MDW 2027-01-22 18:01:00.

2027-01-18 → 2027-01-24 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-24 18:30:00 → MDW 2027-01-24 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-24 · Axel-exclusive $390.00

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

2027-01-18 → 2027-01-25 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-25 17:55:00 → MDW 2027-01-25 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-25 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-25 13:04:00 → MDW 2027-01-25 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-25 13:04:00 → DTW 2027-01-25 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-25 17:40:00 → MDW 2027-01-25 18:01:00.

2027-01-18 → 2027-01-26 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-26 17:55:00 → MDW 2027-01-26 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-26 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-26 13:04:00 → MDW 2027-01-26 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-26 13:04:00 → DTW 2027-01-26 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-26 17:40:00 → MDW 2027-01-26 18:01:00.

2027-01-18 → 2027-01-28 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-28 17:55:00 → MDW 2027-01-28 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-28 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-28 13:04:00 → MDW 2027-01-28 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-28 13:04:00 → DTW 2027-01-28 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-28 17:40:00 → MDW 2027-01-28 18:01:00.

2027-01-18 → 2027-01-29 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-29 18:30:00 → MDW 2027-01-29 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-29 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-29 13:04:00 → MDW 2027-01-29 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-29 13:04:00 → DTW 2027-01-29 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-29 17:40:00 → MDW 2027-01-29 18:01:00.

2027-01-18 → 2027-01-30 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN2939: BOS 2027-01-30 12:20:00 → MDW 2027-01-30 14:05:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-01-30 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-30 13:04:00 → MDW 2027-01-30 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-30 13:04:00 → DTW 2027-01-30 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-30 17:40:00 → MDW 2027-01-30 18:01:00.

2027-01-18 → 2027-02-01 · Axel-exclusive $290.00

• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-02-01 17:55:00 → MDW 2027-02-01 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-18 → 2027-02-01 · Axel-exclusive $390.00

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-18 10:24:00 → BOS 2027-01-18 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-18 10:24:00 → MSP 2027-01-18 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-18 13:09:00 → BOS 2027-01-18 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-02-01 13:04:00 → MDW 2027-02-01 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-01 13:04:00 → DTW 2027-02-01 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-01 17:40:00 → MDW 2027-02-01 18:01:00.

Explore this route

• All dates for this route
• Jan 17, 2027 · Return options
• Jan 19, 2027 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (MDW) to Boston (BOS) · Jan 18, 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 Boston 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.
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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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