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Route overview: Boston to Chicago (ORD) flight deals

Boston (BOS) to Chicago (ORD), Jan 24, 2027 – Feb 3, 2027: from $252 round trip

Boston (BOS) to Chicago (ORD), Jan 24, 2027 – Feb 3, 2027: from $252 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $252 round trip, Axel-exclusive, JetBlue Airways, nonstop, Jan 24, 2027 – Feb 3, 2027, 1 adult, economy, checked Oct 29, 2026.

BOS → ORD1 adulteconomyRound trip

14 flight options · 5 airlines

Nonstop flights

Sun, Jan 24 – Wed, Feb 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, Jan 24 – Wed, Feb 3

American Airlines
10:24 amBOS
3h 11m
Nonstop
12:35 pmORD
American Airlines
6:00 amORD
2h 33m
Nonstop
9:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

United Airlines
4:54 pmBOS
3h 6m
Nonstop
7:00 pmORD
United Airlines
10:30 amORD
2h 25m
Nonstop
1:55 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 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.

Sun, Jan 24 – Wed, Feb 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, Jan 24 – Wed, Feb 3

United Airlines
5:45 amBOS
3h 6m
Nonstop
7:51 amORD
United Airlines
10:30 amORD
2h 25m
Nonstop
1:55 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

American Airlines
1:27 pmBOS
3h 12m
Nonstop
3:39 pmORD
American Airlines
6:00 amORD
2h 33m
Nonstop
9:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

Delta Air Lines
8:10 pmBOS
2h 54m
Nonstop
10:04 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.

One-stop flights

Sun, Jan 24 – Wed, Feb 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, Jan 24 – Wed, Feb 3

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
6:00 amORD
2h 33m
Nonstop
9:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
6:00 amORD
2h 33m
Nonstop
9:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

American Airlines
10:00 amBOS
4h 59m
SYR · 1h 8m
1:59 pmORD
American Airlines
6:00 amORD
2h 33m
Nonstop
9:33 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
10:30 amORD
2h 25m
Nonstop
1:55 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Jan 24 – Wed, Feb 3

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
10:30 amORD
2h 25m
Nonstop
1:55 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Jan 24 – Feb 3, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $784 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $586 · 5★ Nobu Hotel Chicago $3,614

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BOS ⇄ ORD

Economy

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Explore this route

All dates for this routeJan 23, 2027 · Return optionsJan 25, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Boston (BOS) to Chicago (ORD), Jan 24, 2027 – Feb 3, 2027: from $252 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $252 round trip, Axel-exclusive, JetBlue Airways, nonstop, Jan 24, 2027 – Feb 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)
2027-01-24 → 2027-02-03JetBlue AirwaysB6111 / B6101209:59:00→12:00:00 3h 01m nonstop · 17:46:00→21:14:00 2h 28m nonstopAxel-exclusive $251.762026-10-29T00:52:35Z
2027-01-24 → 2027-02-03American AirlinesAA2015 / AA64010:24:00→12:35:00 3h 11m nonstop · 06:00:00→09:33:00 2h 33m nonstopAxel-exclusive $275.502026-10-29T00:52:35Z
2027-01-24 → 2027-02-03United AirlinesUA2040 / UA160616:54:00→19:00:00 3h 06m nonstop · 10:30:00→13:55:00 2h 25m nonstopAxel-exclusive $275.502026-10-29T00:52:35Z
2027-01-24 → 2027-02-03Delta Air LinesDL2570 / DL568807:30:00→09:35:00 3h 05m nonstop · 07:05:00→10:33:00 2h 28m nonstopAxel-exclusive $285.002026-10-29T00:52:35Z
2027-01-24 → 2027-02-03Air 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 $418.002026-10-29T00:52:35Z
2027-01-24 → 2027-02-03JetBlue AirwaysB6811 / B6101216:45:00→18:58:00 3h 13m nonstop · 17:46:00→21:14:00 2h 28m nonstopAxel-exclusive $251.762026-10-29T00:52:35Z
2027-01-24 → 2027-02-03United AirlinesUA1414 / UA160605:45:00→07:51:00 3h 06m nonstop · 10:30:00→13:55:00 2h 25m nonstopAxel-exclusive $275.502026-10-29T00:52:35Z
2027-01-24 → 2027-02-03American AirlinesAA653 / AA64013:27:00→15:39:00 3h 12m nonstop · 06:00:00→09:33:00 2h 33m nonstopAxel-exclusive $275.502026-10-29T00:52:35Z
2027-01-24 → 2027-02-03Delta Air LinesDL5606 / DL568820:10:00→22:04:00 2h 54m nonstop · 07:05:00→10:33:00 2h 28m nonstopAxel-exclusive $285.002026-10-29T00:52:35Z
2027-01-24 → 2027-02-03American AirlinesAA4798 + AA3177 / AA64015:45:00→20:30:00 5h 45m 1 stop via PHL · 06:00:00→09:33:00 2h 33m nonstopAxel-exclusive $285.002026-10-29T00:52:35Z
2027-01-24 → 2027-02-03American AirlinesAA4609 + AA4733 / AA64010:07:00→15:14:00 6h 07m 1 stop via CVG · 06:00:00→09:33:00 2h 33m nonstopAxel-exclusive $285.002026-10-29T00:52:35Z
2027-01-24 → 2027-02-03American AirlinesAA4133 + AA4390 / AA64010:00:00→13:59:00 4h 59m 1 stop via SYR · 06:00:00→09:33:00 2h 33m nonstopAxel-exclusive $285.002026-10-29T00:52:35Z
2027-01-24 → 2027-02-03United AirlinesUA546 + UA703 / UA160615:42:00→20:06:00 5h 24m 1 stop via EWR · 10:30:00→13:55:00 2h 25m nonstopAxel-exclusive $287.382026-10-29T00:52:35Z
2027-01-24 → 2027-02-03United AirlinesUA721 + UA2497 / UA160614:40:00→19:05:00 5h 25m 1 stop via IAD · 10:30:00→13:55:00 2h 25m nonstopAxel-exclusive $287.382026-10-29T00:52:35Z

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

2027-01-24 → 2027-02-03 · Axel-exclusive $251.76

  • JetBlue Airways B6111: BOS 2027-01-24 09:59:00 → ORD 2027-01-24 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2027-02-03 17:46:00 → BOS 2027-02-03 21:14:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

  • American Airlines AA2015: BOS 2027-01-24 10:24:00 → ORD 2027-01-24 12:35:00; nonstop; 191 minutes. Local airport times.
  • American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

  • United Airlines UA2040: BOS 2027-01-24 16:54:00 → ORD 2027-01-24 19:00:00; nonstop; 186 minutes. Local airport times.
  • United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

  • Delta Air Lines DL2570: BOS 2027-01-24 07:30:00 → ORD 2027-01-24 09:35:00; nonstop; 185 minutes. Local airport times.
  • Delta Air Lines DL5688: ORD 2027-02-03 07:05:00 → BOS 2027-02-03 10:33:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $418.00

  • Air Canada AC8695 / AC511: BOS 2027-01-24 15:10:00 → ORD 2027-01-24 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2027-01-24 15:10:00 → YYZ 2027-01-24 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2027-01-24 18:55:00 → ORD 2027-01-24 19:58:00.
  • Air Canada AC508 / AC772: ORD 2027-02-03 16:30:00 → BOS 2027-02-03 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2027-02-03 16:30:00 → YYZ 2027-02-03 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2027-02-03 20:55:00 → BOS 2027-02-03 22:37:00.

2027-01-24 → 2027-02-03 · Axel-exclusive $251.76

  • JetBlue Airways B6811: BOS 2027-01-24 16:45:00 → ORD 2027-01-24 18:58:00; nonstop; 193 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2027-02-03 17:46:00 → BOS 2027-02-03 21:14:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

  • United Airlines UA1414: BOS 2027-01-24 05:45:00 → ORD 2027-01-24 07:51:00; nonstop; 186 minutes. Local airport times.
  • United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

  • American Airlines AA653: BOS 2027-01-24 13:27:00 → ORD 2027-01-24 15:39:00; nonstop; 192 minutes. Local airport times.
  • American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

  • Delta Air Lines DL5606: BOS 2027-01-24 20:10:00 → ORD 2027-01-24 22:04:00; nonstop; 174 minutes. Local airport times.
  • Delta Air Lines DL5688: ORD 2027-02-03 07:05:00 → BOS 2027-02-03 10:33:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

  • American Airlines AA4798 / AA3177: BOS 2027-01-24 15:45:00 → ORD 2027-01-24 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2027-01-24 15:45:00 → PHL 2027-01-24 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2027-01-24 18:35:00 → ORD 2027-01-24 20:30:00.
  • American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

  • American Airlines AA4609 / AA4733: BOS 2027-01-24 10:07:00 → ORD 2027-01-24 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2027-01-24 10:07:00 → CVG 2027-01-24 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2027-01-24 14:34:00 → ORD 2027-01-24 15:14:00.
  • American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

  • American Airlines AA4133 / AA4390: BOS 2027-01-24 10:00:00 → ORD 2027-01-24 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
    • AA4133: BOS 2027-01-24 10:00:00 → SYR 2027-01-24 11:23:00; layover at SYR: 68 minutes.
    • AA4390: SYR 2027-01-24 12:31:00 → ORD 2027-01-24 13:59:00.
  • American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $287.38

  • United Airlines UA546 / UA703: BOS 2027-01-24 15:42:00 → ORD 2027-01-24 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2027-01-24 15:42:00 → EWR 2027-01-24 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2027-01-24 18:10:00 → ORD 2027-01-24 20:06:00.
  • United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $287.38

  • United Airlines UA721 / UA2497: BOS 2027-01-24 14:40:00 → ORD 2027-01-24 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2027-01-24 14:40:00 → IAD 2027-01-24 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2027-01-24 17:39:00 → ORD 2027-01-24 19:05:00.
  • United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 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) · Jan 24, 2027 · return Feb 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.