Boston (BOS) to Chicago (MDW), Jan 6, 2027: round trips from $225, one way from $95

Boston (BOS) to Chicago (MDW), Jan 6, 2027: round trips from $225, one way from $95 on Axel, checked Oct 29, 2026. Lowest published fares: $225 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Jan 6–7, 2027; $95 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 6, 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 6–7, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $210 total
• Hotels in Chicago for these nights (Jan 6–8, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $147 total · 4★ Warwick Allerton - Chicago, $177 total · 5★ Sofitel Chicago Magnificent Mile, $409 total
• Hotels in Chicago for these nights (Jan 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $241 total · 4★ Warwick Allerton - Chicago, $266 total · 5★ Sofitel Chicago Magnificent Mile, $659 total
• Hotels in Chicago for these nights (Jan 6–10, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $316 total · 4★ Warwick Allerton - Chicago, $362 total · 5★ Sofitel Chicago Magnificent Mile, $917 total
• Hotels in Chicago for these nights (Jan 6–11, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $391 total · 4★ Warwick Allerton - Chicago, $447 total · 5★ Sofitel Chicago Magnificent Mile, $1,136 total
• Hotels in Chicago for these nights (Jan 6–12, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $476 total · 4★ Warwick Allerton - Chicago, $532 total · 5★ Sofitel Chicago Magnificent Mile, $1,390 total
• Hotels in Chicago for these nights (Jan 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $551 total · 4★ Warwick Allerton - Chicago, $619 total · 5★ Sofitel Chicago Magnificent Mile, $1,644 total
• Hotels in Chicago for these nights (Jan 6–14, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $626 total · 4★ Warwick Allerton - Chicago, $707 total · 5★ Sofitel Chicago Magnificent Mile, $1,898 total
• Hotels in Chicago for these nights (Jan 6–15, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $701 total · 4★ Warwick Allerton - Chicago, $796 total · 5★ Sofitel Chicago Magnificent Mile, $2,112 total
• Hotels in Chicago for these nights (Jan 6–16, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $784 total · 4★ Warwick Allerton - Chicago, $887 total · 5★ Sofitel Chicago Magnificent Mile, $2,327 total
• Hotels in Chicago for these nights (Jan 6–17, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $859 total · 4★ Warwick Allerton - Chicago, $983 total · 5★ Sofitel Chicago Magnificent Mile, $2,546 total
• Hotels in Chicago for these nights (Jan 6–18, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $934 total · 4★ Warwick Allerton - Chicago, $1,073 total · 5★ Sofitel Chicago Magnificent Mile, $2,769 total
• Hotels in Chicago for these nights (Jan 6–19, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,009 total · 4★ Warwick Allerton - Chicago, $1,165 total · 5★ Sofitel Chicago Magnificent Mile, $3,023 total
• Hotels in Chicago for these nights (Jan 6–20, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,084 total · 4★ Warwick Allerton - Chicago, $1,249 total · 5★ Sofitel Chicago Magnificent Mile, $3,276 total

All hotels in Chicago

Route overview: Boston to Chicago (MDW) flight deals

2027-01-06 · one way · Axel-exclusive $95.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.

2027-01-06 · one way · Axel-exclusive $150.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.

2027-01-06 → 2027-01-07 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2902: MDW 2027-01-07 19:35:00 → BOS 2027-01-07 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-06 → 2027-01-07 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2902: MDW 2027-01-07 19:35:00 → BOS 2027-01-07 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-06 → 2027-01-08 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-08 13:00:00 → BOS 2027-01-08 16:10:00; nonstop; 130 minutes. Local airport times.

2027-01-06 → 2027-01-08 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-08 13:00:00 → BOS 2027-01-08 16:10:00; nonstop; 130 minutes. Local airport times.

2027-01-06 → 2027-01-09 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN4113: MDW 2027-01-09 07:40:00 → BOS 2027-01-09 10:55:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-09 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN4113: MDW 2027-01-09 07:40:00 → BOS 2027-01-09 10:55:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-10 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN249: MDW 2027-01-10 20:40:00 → BOS 2027-01-10 23:55:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-10 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN249: MDW 2027-01-10 20:40:00 → BOS 2027-01-10 23:55:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-12 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-12 13:15:00 → BOS 2027-01-12 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-06 → 2027-01-12 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-12 13:15:00 → BOS 2027-01-12 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-06 → 2027-01-13 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-13 13:05:00 → BOS 2027-01-13 16:20:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-13 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-13 13:05:00 → BOS 2027-01-13 16:20:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-14 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-06 → 2027-01-14 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-06 → 2027-01-16 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 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.

2027-01-06 → 2027-01-16 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 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.

2027-01-06 → 2027-01-17 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN249: MDW 2027-01-17 20:40:00 → BOS 2027-01-17 23:55:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-17 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN249: MDW 2027-01-17 20:40:00 → BOS 2027-01-17 23:55:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-18 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.

2027-01-06 → 2027-01-18 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-18 13:00:00 → BOS 2027-01-18 16:10:00; nonstop; 130 minutes. Local airport times.

2027-01-06 → 2027-01-20 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-06 12:15:00 → MDW 2027-01-06 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-06 12:15:00 → ATL 2027-01-06 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-06 16:45:00 → MDW 2027-01-06 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-20 13:05:00 → BOS 2027-01-20 16:20:00; nonstop; 135 minutes. Local airport times.

2027-01-06 → 2027-01-20 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-20 13:05:00 → BOS 2027-01-20 16:20:00; nonstop; 135 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 5, 2027 · Return options
• Jan 7, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (MDW) · Jan 6, 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 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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