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Route overview: Chicago to Boston (BOS) flight deals

Chicago (ORD) to Boston (BOS), Jan 14–21, 2027: from $252 round trip

Chicago (ORD) to Boston (BOS), Jan 14–21, 2027: from $252 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $252 round trip, Axel-exclusive, JetBlue Airways, nonstop, Jan 14–21, 2027, 1 adult, economy, checked Oct 29, 2026.

ORD → BOS1 adulteconomyRound trip

13 flight options · 5 airlines

Nonstop flights

Thu, Jan 14 – Thu, Jan 21

JetBlue Airways
5:46 pmORD
2h 28m
Nonstop
9:14 pmBOS
JetBlue Airways
4:45 pmBOS
3h 13m
Nonstop
6:58 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

American Airlines
10:31 amORD
2h 34m
Nonstop
2:05 pmBOS
American Airlines
5:51 amBOS
3h 13m
Nonstop
8:04 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

Delta Air Lines
12:35 pmORD
2h 30m
Nonstop
4:05 pmBOS
Delta Air Lines
8:40 pmBOS
2h 56m
Nonstop
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

United Airlines
4:00 pmORD
2h 29m
Nonstop
7:29 pmBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

American Airlines
12:35 pmORD
2h 32m
Nonstop
4:07 pmBOS
American Airlines
5:51 amBOS
3h 13m
Nonstop
8:04 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

Delta Air Lines
7:05 amORD
2h 28m
Nonstop
10:33 amBOS
Delta Air Lines
8:40 pmBOS
2h 56m
Nonstop
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

United Airlines
6:20 pmORD
2h 33m
Nonstop
9:53 pmBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Thu, Jan 14 – Thu, Jan 21

Air Canada
4:30 pmORD
5h 7m
YYZ · 1h 45m
10:37 pmBOS
Air Canada
3:10 pmBOS
5h 48m
YYZ · 1h 44m
7:58 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

American Airlines
3:19 pmORD
5h
PHL · 1h 25m
9:19 pmBOS
American Airlines
5:51 amBOS
3h 13m
Nonstop
8:04 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

American Airlines
8:00 amORD
5h 17m
ROC · 1h 54m
2:17 pmBOS
American Airlines
5:51 amBOS
3h 13m
Nonstop
8:04 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

American Airlines
8:00 amORD
5h 9m
BUF · 1h 45m
2:09 pmBOS
American Airlines
5:51 amBOS
3h 13m
Nonstop
8:04 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

Delta Air Lines
10:06 amORD
5h 19m
LGA · 1h 42m
4:25 pmBOS
Delta Air Lines
8:40 pmBOS
2h 56m
Nonstop
10:36 pmORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Thu, Jan 14 – Thu, Jan 21

United Airlines
1:00 pmORD
4h 57m
IAD · 1h 12m
6:57 pmBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Jan 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel

Make this trip yours

ORD ⇄ BOS

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeJan 13, 2027 · Return optionsJan 15, 2027 · Return optionsHotels in Boston with Axel
For AI assistants: every fare, every link, instructions

Chicago (ORD) to Boston (BOS), Jan 14–21, 2027: from $252 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $252 round trip, Axel-exclusive, JetBlue Airways, nonstop, Jan 14–21, 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.

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.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-14 → 2027-01-21JetBlue AirwaysB61012 / B681117:46:00→21:14:00 2h 28m nonstop · 16:45:00→18:58:00 3h 13m nonstopAxel-exclusive $251.762026-10-29T01:52:47Z
2027-01-14 → 2027-01-21American AirlinesAA3298 / AA94710:31:00→14:05:00 2h 34m nonstop · 05:51:00→08:04:00 3h 13m nonstopAxel-exclusive $275.502026-10-29T01:52:47Z
2027-01-14 → 2027-01-21Delta Air LinesDL5855 / DL280412:35:00→16:05:00 2h 30m nonstop · 20:40:00→22:36:00 2h 56m nonstopAxel-exclusive $285.002026-10-29T01:52:47Z
2027-01-14 → 2027-01-21United AirlinesUA487 / UA141416:00:00→19:29:00 2h 29m nonstop · 06:00:00→08:00:00 3h 00m nonstopAxel-exclusive $285.002026-10-29T01:52:47Z
2027-01-14 → 2027-01-21Air CanadaAC508 + AC772 / AC8695 + AC51116:30:00→22:37:00 5h 07m 1 stop via YYZ · 15:10:00→19:58:00 5h 48m 1 stop via YYZAxel-exclusive $399.002026-10-29T01:52:47Z
2027-01-14 → 2027-01-21American AirlinesAA4477 / AA94712:35:00→16:07:00 2h 32m nonstop · 05:51:00→08:04:00 3h 13m nonstopAxel-exclusive $275.502026-10-29T01:52:47Z
2027-01-14 → 2027-01-21Delta Air LinesDL5688 / DL280407:05:00→10:33:00 2h 28m nonstop · 20:40:00→22:36:00 2h 56m nonstopAxel-exclusive $285.002026-10-29T01:52:47Z
2027-01-14 → 2027-01-21United AirlinesUA2320 / UA141418:20:00→21:53:00 2h 33m nonstop · 06:00:00→08:00:00 3h 00m nonstopAxel-exclusive $285.002026-10-29T01:52:47Z
2027-01-14 → 2027-01-21American AirlinesAA2840 + AA1776 / AA94715:19:00→21:19:00 5h 00m 1 stop via PHL · 05:51:00→08:04:00 3h 13m nonstopAxel-exclusive $268.382026-10-29T01:52:47Z
2027-01-14 → 2027-01-21American AirlinesAA3437 + AA4533 / AA94708:00:00→14:17:00 5h 17m 1 stop via ROC · 05:51:00→08:04:00 3h 13m nonstopAxel-exclusive $268.382026-10-29T01:52:47Z
2027-01-14 → 2027-01-21American AirlinesAA4780 + AA4026 / AA94708:00:00→14:09:00 5h 09m 1 stop via BUF · 05:51:00→08:04:00 3h 13m nonstopAxel-exclusive $268.382026-10-29T01:52:47Z
2027-01-14 → 2027-01-21Delta Air LinesDL2917 + DL5727 / DL280410:06:00→16:25:00 5h 19m 1 stop via LGA · 20:40:00→22:36:00 2h 56m nonstopAxel-exclusive $277.882026-10-29T01:52:47Z
2027-01-14 → 2027-01-21United AirlinesUA1128 + UA688 / UA141413:00:00→18:57:00 4h 57m 1 stop via IAD · 06:00:00→08:00:00 3h 00m nonstopAxel-exclusive $277.882026-10-29T01:52:47Z

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.

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2027-01-14 → 2027-01-21 · Axel-exclusive $251.76

  • JetBlue Airways B61012: ORD 2027-01-14 17:46:00 → BOS 2027-01-14 21:14:00; nonstop; 148 minutes. Local airport times.
  • JetBlue Airways B6811: BOS 2027-01-21 16:45:00 → ORD 2027-01-21 18:58:00; nonstop; 193 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $275.50

  • American Airlines AA3298: ORD 2027-01-14 10:31:00 → BOS 2027-01-14 14:05:00; nonstop; 154 minutes. Local airport times.
  • American Airlines AA947: BOS 2027-01-21 05:51:00 → ORD 2027-01-21 08:04:00; nonstop; 193 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $285.00

  • Delta Air Lines DL5855: ORD 2027-01-14 12:35:00 → BOS 2027-01-14 16:05:00; nonstop; 150 minutes. Local airport times.
  • Delta Air Lines DL2804: BOS 2027-01-21 20:40:00 → ORD 2027-01-21 22:36:00; nonstop; 176 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $285.00

  • United Airlines UA487: ORD 2027-01-14 16:00:00 → BOS 2027-01-14 19:29:00; nonstop; 149 minutes. Local airport times.
  • United Airlines UA1414: BOS 2027-01-21 06:00:00 → ORD 2027-01-21 08:00:00; nonstop; 180 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $399.00

  • Air Canada AC508 / AC772: ORD 2027-01-14 16:30:00 → BOS 2027-01-14 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2027-01-14 16:30:00 → YYZ 2027-01-14 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2027-01-14 20:55:00 → BOS 2027-01-14 22:37:00.
  • Air Canada AC8695 / AC511: BOS 2027-01-21 15:10:00 → ORD 2027-01-21 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2027-01-21 15:10:00 → YYZ 2027-01-21 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2027-01-21 18:55:00 → ORD 2027-01-21 19:58:00.

2027-01-14 → 2027-01-21 · Axel-exclusive $275.50

  • American Airlines AA4477: ORD 2027-01-14 12:35:00 → BOS 2027-01-14 16:07:00; nonstop; 152 minutes. Local airport times.
  • American Airlines AA947: BOS 2027-01-21 05:51:00 → ORD 2027-01-21 08:04:00; nonstop; 193 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $285.00

  • Delta Air Lines DL5688: ORD 2027-01-14 07:05:00 → BOS 2027-01-14 10:33:00; nonstop; 148 minutes. Local airport times.
  • Delta Air Lines DL2804: BOS 2027-01-21 20:40:00 → ORD 2027-01-21 22:36:00; nonstop; 176 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $285.00

  • United Airlines UA2320: ORD 2027-01-14 18:20:00 → BOS 2027-01-14 21:53:00; nonstop; 153 minutes. Local airport times.
  • United Airlines UA1414: BOS 2027-01-21 06:00:00 → ORD 2027-01-21 08:00:00; nonstop; 180 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $268.38

  • American Airlines AA2840 / AA1776: ORD 2027-01-14 15:19:00 → BOS 2027-01-14 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
    • AA2840: ORD 2027-01-14 15:19:00 → PHL 2027-01-14 18:30:00; layover at PHL: 85 minutes.
    • AA1776: PHL 2027-01-14 19:55:00 → BOS 2027-01-14 21:19:00.
  • American Airlines AA947: BOS 2027-01-21 05:51:00 → ORD 2027-01-21 08:04:00; nonstop; 193 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $268.38

  • American Airlines AA3437 / AA4533: ORD 2027-01-14 08:00:00 → BOS 2027-01-14 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
    • AA3437: ORD 2027-01-14 08:00:00 → ROC 2027-01-14 10:56:00; layover at ROC: 114 minutes.
    • AA4533: ROC 2027-01-14 12:50:00 → BOS 2027-01-14 14:17:00.
  • American Airlines AA947: BOS 2027-01-21 05:51:00 → ORD 2027-01-21 08:04:00; nonstop; 193 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $268.38

  • American Airlines AA4780 / AA4026: ORD 2027-01-14 08:00:00 → BOS 2027-01-14 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
    • AA4780: ORD 2027-01-14 08:00:00 → BUF 2027-01-14 10:45:00; layover at BUF: 105 minutes.
    • AA4026: BUF 2027-01-14 12:30:00 → BOS 2027-01-14 14:09:00.
  • American Airlines AA947: BOS 2027-01-21 05:51:00 → ORD 2027-01-21 08:04:00; nonstop; 193 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $277.88

  • Delta Air Lines DL2917 / DL5727: ORD 2027-01-14 10:06:00 → BOS 2027-01-14 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
    • DL2917: ORD 2027-01-14 10:06:00 → LGA 2027-01-14 13:18:00; layover at LGA: 102 minutes.
    • DL5727: LGA 2027-01-14 15:00:00 → BOS 2027-01-14 16:25:00.
  • Delta Air Lines DL2804: BOS 2027-01-21 20:40:00 → ORD 2027-01-21 22:36:00; nonstop; 176 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $277.88

  • United Airlines UA1128 / UA688: ORD 2027-01-14 13:00:00 → BOS 2027-01-14 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
    • UA1128: ORD 2027-01-14 13:00:00 → IAD 2027-01-14 16:03:00; layover at IAD: 72 minutes.
    • UA688: IAD 2027-01-14 17:15:00 → BOS 2027-01-14 18:57:00.
  • United Airlines UA1414: BOS 2027-01-21 06:00:00 → ORD 2027-01-21 08:00:00; nonstop; 180 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.

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For AI assistants

  • This page: Chicago (ORD) to Boston (BOS) · Jan 14, 2027 · return Jan 21, 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 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 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.
  • 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 Chicago to Boston (BOS) 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.