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Route overview: Boston to Chicago (ORD) flight deals

Boston (BOS) to Chicago (ORD), Dec 20, 2026 – Jan 3, 2027: from $329 round trip

Boston (BOS) to Chicago (ORD), Dec 20, 2026 – Jan 3, 2027: from $329 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $329 round trip, Axel-exclusive, JetBlue Airways, nonstop, Dec 20, 2026 – Jan 3, 2027, 1 adult, economy, checked Oct 29, 2026.

BOS → ORD1 adulteconomyRound trip

14 flight options · 5 airlines

Nonstop flights

Sun, Dec 20 – Sun, Jan 3

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

American Airlines
1:27 pmBOS
3h 12m
Nonstop
3:39 pmORD
American Airlines
6:15 pmORD
2h 36m
Nonstop
9:51 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

United Airlines
5:45 amBOS
3h 6m
Nonstop
7:51 amORD
United Airlines
6:50 amORD
2h 27m
Nonstop
10:17 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

Delta Air Lines
2:55 pmBOS
3h 6m
Nonstop
5:01 pmORD
Delta Air Lines
7:05 amORD
2h 28m
Nonstop
10:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

JetBlue Airways
9:59 amBOS
3h 1m
Nonstop
12:00 pmORD
JetBlue Airways
5:46 pmORD
2h 28m
Nonstop
9:14 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

American Airlines
10:24 amBOS
3h 11m
Nonstop
12:35 pmORD
American Airlines
6:15 pmORD
2h 36m
Nonstop
9:51 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

United Airlines
4:45 pmBOS
3h 3m
Nonstop
6:48 pmORD
United Airlines
6:50 amORD
2h 27m
Nonstop
10:17 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

Delta Air Lines
7:30 amBOS
3h 5m
Nonstop
9:35 amORD
Delta Air Lines
7:05 amORD
2h 28m
Nonstop
10:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sun, Dec 20 – Sun, Jan 3

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

American Airlines
10:00 amBOS
4h 59m
SYR · 1h 8m
1:59 pmORD
American Airlines
6:15 pmORD
2h 36m
Nonstop
9:51 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
6:15 pmORD
2h 36m
Nonstop
9:51 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
6:15 pmORD
2h 36m
Nonstop
9:51 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
6:50 amORD
2h 27m
Nonstop
10:17 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Jan 3

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
6:50 amORD
2h 27m
Nonstop
10:17 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Dec 20 – Jan 3, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,501 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $807 · 5★ Sofitel Chicago Magnificent Mile $3,466

Make this trip yours

BOS ⇄ ORD

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 routeDec 19, 2026 · Return optionsDec 21, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Boston (BOS) to Chicago (ORD), Dec 20, 2026 – Jan 3, 2027: from $329 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $329 round trip, Axel-exclusive, JetBlue Airways, nonstop, Dec 20, 2026 – Jan 3, 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)
2026-12-20 → 2027-01-03JetBlue AirwaysB6811 / B6101216:45:00→18:58:00 3h 13m nonstop · 17:46:00→21:14:00 2h 28m nonstopAxel-exclusive $328.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03American AirlinesAA653 / AA46913:27:00→15:39:00 3h 12m nonstop · 18:15:00→21:51:00 2h 36m nonstopAxel-exclusive $359.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03United AirlinesUA1414 / UA221305:45:00→07:51:00 3h 06m nonstop · 06:50:00→10:17:00 2h 27m nonstopAxel-exclusive $359.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03Delta Air LinesDL5611 / DL568814:55:00→17:01:00 3h 06m nonstop · 07:05:00→10:33:00 2h 28m nonstopAxel-exclusive $372.002026-10-29T00:52:35Z
2026-12-20 → 2027-01-03Air CanadaAC8695 + AC511 / AC508 + AC77215:10:00→19:58:00 5h 48m 1 stop via YYZ · 16:30:00→22:37:00 5h 07m 1 stop via YYZAxel-exclusive $545.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03JetBlue AirwaysB6111 / B6101209:59:00→12:00:00 3h 01m nonstop · 17:46:00→21:14:00 2h 28m nonstopAxel-exclusive $328.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03American AirlinesAA2015 / AA46910:24:00→12:35:00 3h 11m nonstop · 18:15:00→21:51:00 2h 36m nonstopAxel-exclusive $359.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03United AirlinesUA2040 / UA221316:45:00→18:48:00 3h 03m nonstop · 06:50:00→10:17:00 2h 27m nonstopAxel-exclusive $359.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03Delta Air LinesDL2570 / DL568807:30:00→09:35:00 3h 05m nonstop · 07:05:00→10:33:00 2h 28m nonstopAxel-exclusive $372.002026-10-29T00:52:35Z
2026-12-20 → 2027-01-03American AirlinesAA4133 + AA4390 / AA46910:00:00→13:59:00 4h 59m 1 stop via SYR · 18:15:00→21:51:00 2h 36m nonstopAxel-exclusive $372.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03American AirlinesAA4798 + AA3177 / AA46915:45:00→20:30:00 5h 45m 1 stop via PHL · 18:15:00→21:51:00 2h 36m nonstopAxel-exclusive $372.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03American AirlinesAA4609 + AA4733 / AA46910:07:00→15:14:00 6h 07m 1 stop via CVG · 18:15:00→21:51:00 2h 36m nonstopAxel-exclusive $372.602026-10-29T00:52:35Z
2026-12-20 → 2027-01-03United AirlinesUA546 + UA703 / UA221315:42:00→20:06:00 5h 24m 1 stop via EWR · 06:50:00→10:17:00 2h 27m nonstopAxel-exclusive $375.852026-10-29T00:52:35Z
2026-12-20 → 2027-01-03United AirlinesUA721 + UA2497 / UA221314:40:00→19:05:00 5h 25m 1 stop via IAD · 06:50:00→10:17:00 2h 27m nonstopAxel-exclusive $375.852026-10-29T00:52:35Z

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.

All hotels in Chicago

Route overview: Boston to Chicago (ORD) flight deals

2026-12-20 → 2027-01-03 · Axel-exclusive $328.60

  • JetBlue Airways B6811: BOS 2026-12-20 16:45:00 → ORD 2026-12-20 18:58:00; nonstop; 193 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2027-01-03 17:46:00 → BOS 2027-01-03 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $359.60

  • American Airlines AA653: BOS 2026-12-20 13:27:00 → ORD 2026-12-20 15:39:00; nonstop; 192 minutes. Local airport times.
  • American Airlines AA469: ORD 2027-01-03 18:15:00 → BOS 2027-01-03 21:51:00; nonstop; 156 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $359.60

  • United Airlines UA1414: BOS 2026-12-20 05:45:00 → ORD 2026-12-20 07:51:00; nonstop; 186 minutes. Local airport times.
  • United Airlines UA2213: ORD 2027-01-03 06:50:00 → BOS 2027-01-03 10:17:00; nonstop; 147 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $372.00

  • Delta Air Lines DL5611: BOS 2026-12-20 14:55:00 → ORD 2026-12-20 17:01:00; nonstop; 186 minutes. Local airport times.
  • Delta Air Lines DL5688: ORD 2027-01-03 07:05:00 → BOS 2027-01-03 10:33:00; nonstop; 148 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $545.60

  • Air Canada AC8695 / AC511: BOS 2026-12-20 15:10:00 → ORD 2026-12-20 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2026-12-20 15:10:00 → YYZ 2026-12-20 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2026-12-20 18:55:00 → ORD 2026-12-20 19:58:00.
  • Air Canada AC508 / AC772: ORD 2027-01-03 16:30:00 → BOS 2027-01-03 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2027-01-03 16:30:00 → YYZ 2027-01-03 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2027-01-03 20:55:00 → BOS 2027-01-03 22:37:00.

2026-12-20 → 2027-01-03 · Axel-exclusive $328.60

  • JetBlue Airways B6111: BOS 2026-12-20 09:59:00 → ORD 2026-12-20 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2027-01-03 17:46:00 → BOS 2027-01-03 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $359.60

  • American Airlines AA2015: BOS 2026-12-20 10:24:00 → ORD 2026-12-20 12:35:00; nonstop; 191 minutes. Local airport times.
  • American Airlines AA469: ORD 2027-01-03 18:15:00 → BOS 2027-01-03 21:51:00; nonstop; 156 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $359.60

  • United Airlines UA2040: BOS 2026-12-20 16:45:00 → ORD 2026-12-20 18:48:00; nonstop; 183 minutes. Local airport times.
  • United Airlines UA2213: ORD 2027-01-03 06:50:00 → BOS 2027-01-03 10:17:00; nonstop; 147 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $372.00

  • Delta Air Lines DL2570: BOS 2026-12-20 07:30:00 → ORD 2026-12-20 09:35:00; nonstop; 185 minutes. Local airport times.
  • Delta Air Lines DL5688: ORD 2027-01-03 07:05:00 → BOS 2027-01-03 10:33:00; nonstop; 148 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $372.60

  • American Airlines AA4133 / AA4390: BOS 2026-12-20 10:00:00 → ORD 2026-12-20 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
    • AA4133: BOS 2026-12-20 10:00:00 → SYR 2026-12-20 11:23:00; layover at SYR: 68 minutes.
    • AA4390: SYR 2026-12-20 12:31:00 → ORD 2026-12-20 13:59:00.
  • American Airlines AA469: ORD 2027-01-03 18:15:00 → BOS 2027-01-03 21:51:00; nonstop; 156 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $372.60

  • American Airlines AA4798 / AA3177: BOS 2026-12-20 15:45:00 → ORD 2026-12-20 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2026-12-20 15:45:00 → PHL 2026-12-20 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2026-12-20 18:35:00 → ORD 2026-12-20 20:30:00.
  • American Airlines AA469: ORD 2027-01-03 18:15:00 → BOS 2027-01-03 21:51:00; nonstop; 156 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $372.60

  • American Airlines AA4609 / AA4733: BOS 2026-12-20 10:07:00 → ORD 2026-12-20 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2026-12-20 10:07:00 → CVG 2026-12-20 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2026-12-20 14:34:00 → ORD 2026-12-20 15:14:00.
  • American Airlines AA469: ORD 2027-01-03 18:15:00 → BOS 2027-01-03 21:51:00; nonstop; 156 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $375.85

  • United Airlines UA546 / UA703: BOS 2026-12-20 15:42:00 → ORD 2026-12-20 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2026-12-20 15:42:00 → EWR 2026-12-20 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2026-12-20 18:10:00 → ORD 2026-12-20 20:06:00.
  • United Airlines UA2213: ORD 2027-01-03 06:50:00 → BOS 2027-01-03 10:17:00; nonstop; 147 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $375.85

  • United Airlines UA721 / UA2497: BOS 2026-12-20 14:40:00 → ORD 2026-12-20 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2026-12-20 14:40:00 → IAD 2026-12-20 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2026-12-20 17:39:00 → ORD 2026-12-20 19:05:00.
  • United Airlines UA2213: ORD 2027-01-03 06:50:00 → BOS 2027-01-03 10:17:00; nonstop; 147 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: Boston (BOS) to Chicago (ORD) · Dec 20, 2026 · return Jan 3, 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 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 Boston to Chicago (ORD) 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.