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Route overview: Boston to Chicago (ORD) flight deals

Boston → Chicago

Feb 5, 2027 · return Feb 8, 2027

BOS → ORD1 adulteconomyRound trip

14 flight options · 5 airlines

Nonstop flights

Fri, Feb 5 – Mon, Feb 8

JetBlue Airways
2:40 pmBOS
3h
Nonstop
4:40 pmORD
JetBlue Airways
5:46 pmORD
2h 28m
Nonstop
9:14 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

United Airlines
8:25 pmBOS
3h 4m
Nonstop
10:29 pmORD
United Airlines
6:05 amORD
2h 18m
Nonstop
9:23 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

American Airlines
12:16 pmBOS
3h 12m
Nonstop
2:28 pmORD
American Airlines
6:00 amORD
2h 29m
Nonstop
9:29 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

Delta Air Lines
8:59 pmBOS
2h 58m
Nonstop
10:57 pmORD
Delta Air Lines
3:05 pmORD
2h 31m
Nonstop
6:36 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

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

Fri, Feb 5 – Mon, Feb 8

American Airlines
10:24 amBOS
3h 11m
Nonstop
12:35 pmORD
American Airlines
6:00 amORD
2h 29m
Nonstop
9:29 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

United Airlines
2:58 pmBOS
3h 2m
Nonstop
5:00 pmORD
United Airlines
6:05 amORD
2h 18m
Nonstop
9:23 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

Delta Air Lines
4:35 pmBOS
3h 10m
Nonstop
6:45 pmORD
Delta Air Lines
3:05 pmORD
2h 31m
Nonstop
6:36 pmBOS

Round-trip total · 1 adult · Taxes included

One-stop flights

Fri, Feb 5 – Mon, Feb 8

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

Fri, Feb 5 – Mon, Feb 8

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
6:00 amORD
2h 29m
Nonstop
9:29 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
6:00 amORD
2h 29m
Nonstop
9:29 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

American Airlines
10:00 amBOS
4h 59m
SYR · 1h 8m
1:59 pmORD
American Airlines
6:00 amORD
2h 29m
Nonstop
9:29 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
6:05 amORD
2h 18m
Nonstop
9:23 amBOS

Round-trip total · 1 adult · Taxes included

Fri, Feb 5 – Mon, Feb 8

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
6:05 amORD
2h 18m
Nonstop
9:23 amBOS

Round-trip total · 1 adult · Taxes included

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 routeFeb 4, 2027 · Return optionsFeb 6, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

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 datesAirlineFlightsTotal pricePrice issued (UTC)
2027-02-05 → 2027-02-08JetBlue AirwaysB6611 / B61012Axel-exclusive $251.762026-10-29T00:52:35Z
2027-02-05 → 2027-02-08United AirlinesUA2433 / UA1186Axel-exclusive $275.502026-10-29T00:52:35Z
2027-02-05 → 2027-02-08American AirlinesAA581 / AA1951Axel-exclusive $275.502026-10-29T00:52:35Z
2027-02-05 → 2027-02-08Delta Air LinesDL2804 / DL2816Axel-exclusive $285.002026-10-29T00:52:35Z
2027-02-05 → 2027-02-08Air CanadaAC8695 + AC511 / AC508 + AC772Axel-exclusive $418.002026-10-29T00:52:35Z
2027-02-05 → 2027-02-08JetBlue AirwaysB6111 / B61012Axel-exclusive $251.762026-10-29T00:52:35Z
2027-02-05 → 2027-02-08American AirlinesAA2015 / AA1951Axel-exclusive $275.502026-10-29T00:52:35Z
2027-02-05 → 2027-02-08United AirlinesUA2496 / UA1186Axel-exclusive $275.502026-10-29T00:52:35Z
2027-02-05 → 2027-02-08Delta Air LinesDL2646 / DL2816Axel-exclusive $285.002026-10-29T00:52:35Z
2027-02-05 → 2027-02-08American AirlinesAA4609 + AA4733 / AA1951Axel-exclusive $285.002026-10-29T00:52:35Z
2027-02-05 → 2027-02-08American AirlinesAA4798 + AA3177 / AA1951Axel-exclusive $285.002026-10-29T00:52:35Z
2027-02-05 → 2027-02-08American AirlinesAA4133 + AA4390 / AA1951Axel-exclusive $285.002026-10-29T00:52:35Z
2027-02-05 → 2027-02-08United AirlinesUA721 + UA2497 / UA1186Axel-exclusive $287.382026-10-29T00:52:35Z
2027-02-05 → 2027-02-08United AirlinesUA546 + UA703 / UA1186Axel-exclusive $287.382026-10-29T00:52:35Z

Route overview: Boston to Chicago (ORD) flight deals

2027-02-05 → 2027-02-08 · Axel-exclusive $251.76

  • JetBlue Airways B6611: BOS 2027-02-05 14:40:00 → ORD 2027-02-05 16:40:00; nonstop; 180 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2027-02-08 17:46:00 → BOS 2027-02-08 21:14:00; nonstop; 148 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $275.50

  • United Airlines UA2433: BOS 2027-02-05 20:25:00 → ORD 2027-02-05 22:29:00; nonstop; 184 minutes. Local airport times.
  • United Airlines UA1186: ORD 2027-02-08 06:05:00 → BOS 2027-02-08 09:23:00; nonstop; 138 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $275.50

  • American Airlines AA581: BOS 2027-02-05 12:16:00 → ORD 2027-02-05 14:28:00; nonstop; 192 minutes. Local airport times.
  • American Airlines AA1951: ORD 2027-02-08 06:00:00 → BOS 2027-02-08 09:29:00; nonstop; 149 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $285.00

  • Delta Air Lines DL2804: BOS 2027-02-05 20:59:00 → ORD 2027-02-05 22:57:00; nonstop; 178 minutes. Local airport times.
  • Delta Air Lines DL2816: ORD 2027-02-08 15:05:00 → BOS 2027-02-08 18:36:00; nonstop; 151 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $418.00

  • Air Canada AC8695 / AC511: BOS 2027-02-05 15:10:00 → ORD 2027-02-05 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2027-02-05 15:10:00 → YYZ 2027-02-05 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2027-02-05 18:55:00 → ORD 2027-02-05 19:58:00.
  • Air Canada AC508 / AC772: ORD 2027-02-08 16:30:00 → BOS 2027-02-08 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2027-02-08 16:30:00 → YYZ 2027-02-08 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2027-02-08 20:55:00 → BOS 2027-02-08 22:37:00.

2027-02-05 → 2027-02-08 · Axel-exclusive $251.76

  • JetBlue Airways B6111: BOS 2027-02-05 09:59:00 → ORD 2027-02-05 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2027-02-08 17:46:00 → BOS 2027-02-08 21:14:00; nonstop; 148 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $275.50

  • American Airlines AA2015: BOS 2027-02-05 10:24:00 → ORD 2027-02-05 12:35:00; nonstop; 191 minutes. Local airport times.
  • American Airlines AA1951: ORD 2027-02-08 06:00:00 → BOS 2027-02-08 09:29:00; nonstop; 149 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $275.50

  • United Airlines UA2496: BOS 2027-02-05 14:58:00 → ORD 2027-02-05 17:00:00; nonstop; 182 minutes. Local airport times.
  • United Airlines UA1186: ORD 2027-02-08 06:05:00 → BOS 2027-02-08 09:23:00; nonstop; 138 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $285.00

  • Delta Air Lines DL2646: BOS 2027-02-05 16:35:00 → ORD 2027-02-05 18:45:00; nonstop; 190 minutes. Local airport times.
  • Delta Air Lines DL2816: ORD 2027-02-08 15:05:00 → BOS 2027-02-08 18:36:00; nonstop; 151 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $285.00

  • American Airlines AA4609 / AA4733: BOS 2027-02-05 10:07:00 → ORD 2027-02-05 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2027-02-05 10:07:00 → CVG 2027-02-05 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2027-02-05 14:34:00 → ORD 2027-02-05 15:14:00.
  • American Airlines AA1951: ORD 2027-02-08 06:00:00 → BOS 2027-02-08 09:29:00; nonstop; 149 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $285.00

  • American Airlines AA4798 / AA3177: BOS 2027-02-05 15:45:00 → ORD 2027-02-05 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2027-02-05 15:45:00 → PHL 2027-02-05 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2027-02-05 18:35:00 → ORD 2027-02-05 20:30:00.
  • American Airlines AA1951: ORD 2027-02-08 06:00:00 → BOS 2027-02-08 09:29:00; nonstop; 149 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $285.00

  • American Airlines AA4133 / AA4390: BOS 2027-02-05 10:00:00 → ORD 2027-02-05 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
    • AA4133: BOS 2027-02-05 10:00:00 → SYR 2027-02-05 11:23:00; layover at SYR: 68 minutes.
    • AA4390: SYR 2027-02-05 12:31:00 → ORD 2027-02-05 13:59:00.
  • American Airlines AA1951: ORD 2027-02-08 06:00:00 → BOS 2027-02-08 09:29:00; nonstop; 149 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $287.38

  • United Airlines UA721 / UA2497: BOS 2027-02-05 14:40:00 → ORD 2027-02-05 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2027-02-05 14:40:00 → IAD 2027-02-05 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2027-02-05 17:39:00 → ORD 2027-02-05 19:05:00.
  • United Airlines UA1186: ORD 2027-02-08 06:05:00 → BOS 2027-02-08 09:23:00; nonstop; 138 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $287.38

  • United Airlines UA546 / UA703: BOS 2027-02-05 15:42:00 → ORD 2027-02-05 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2027-02-05 15:42:00 → EWR 2027-02-05 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2027-02-05 18:10:00 → ORD 2027-02-05 20:06:00.
  • United Airlines UA1186: ORD 2027-02-08 06:05:00 → BOS 2027-02-08 09:23:00; nonstop; 138 minutes. Local airport times.

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For AI assistants

  • This page: Boston (BOS) to Chicago (ORD) · Feb 5, 2027 · return Feb 8, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.