Flights from Chicago to New England for a week

Flights for your trip

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

2026-11-20 · one way · $140.00

• JetBlue Airways B61012: ORD 2026-11-20 17:46:00 → BOS 2026-11-20 21:14:00; nonstop; 148 minutes. Local airport times.

2026-11-20 · one way · $155.00

• American Airlines AA469: ORD 2026-11-20 17:52:00 → BOS 2026-11-20 21:16:00; nonstop; 144 minutes. Local airport times.

2026-11-20 · one way · $160.00

• Delta Air Lines DL2570: ORD 2026-11-20 10:35:00 → BOS 2026-11-20 13:59:00; nonstop; 144 minutes. Local airport times.

2026-11-20 · one way · $160.00

• United Airlines UA1896: ORD 2026-11-20 12:29:00 → BOS 2026-11-20 15:53:00; nonstop; 144 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $265.00

• JetBlue Airways B61012: ORD 2026-11-20 17:46:00 → BOS 2026-11-20 21:14:00; nonstop; 148 minutes. Local airport times.
• JetBlue Airways B6611: BOS 2026-11-23 14:40:00 → ORD 2026-11-23 16:40:00; nonstop; 180 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $290.00

• American Airlines AA2089: ORD 2026-11-20 06:59:00 → BOS 2026-11-20 10:32:00; nonstop; 153 minutes. Local airport times.
• American Airlines AA1500: BOS 2026-11-23 12:12:00 → ORD 2026-11-23 14:22:00; nonstop; 190 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $300.00

• Delta Air Lines DL5855: ORD 2026-11-20 12:35:00 → BOS 2026-11-20 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL5606: BOS 2026-11-23 20:10:00 → ORD 2026-11-23 22:04:00; nonstop; 174 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $300.00

• United Airlines UA2320: ORD 2026-11-20 18:20:00 → BOS 2026-11-20 21:53:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-11-23 06:00:00 → ORD 2026-11-23 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-20 · one way · $225.00

• Air Canada AC508 / AC772: ORD 2026-11-20 16:30:00 → BOS 2026-11-20 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-20 16:30:00 → YYZ 2026-11-20 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-20 20:55:00 → BOS 2026-11-20 22:37:00.

2026-11-20 → 2026-11-23 · $420.00

• Air Canada AC508 / AC772: ORD 2026-11-20 16:30:00 → BOS 2026-11-20 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-20 16:30:00 → YYZ 2026-11-20 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-20 20:55:00 → BOS 2026-11-20 22:37:00.
• Air Canada AC8695 / AC511: BOS 2026-11-23 15:10:00 → ORD 2026-11-23 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-11-23 15:10:00 → YYZ 2026-11-23 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-11-23 18:55:00 → ORD 2026-11-23 19:58:00.

2026-11-27 → 2026-12-04 · $318.00

• JetBlue Airways B61012: ORD 2026-11-27 17:46:00 → BOS 2026-11-27 21:14:00; nonstop; 148 minutes. Local airport times.
• JetBlue Airways B6611: BOS 2026-12-04 14:40:00 → ORD 2026-12-04 16:40:00; nonstop; 180 minutes. Local airport times.

2026-11-20 · one way · $155.00

• American Airlines AA2089: ORD 2026-11-20 06:59:00 → BOS 2026-11-20 10:32:00; nonstop; 153 minutes. Local airport times.

2026-11-20 · one way · $160.00

• Delta Air Lines DL5855: ORD 2026-11-20 12:35:00 → BOS 2026-11-20 16:05:00; nonstop; 150 minutes. Local airport times.

2026-11-20 · one way · $160.00

• United Airlines UA2320: ORD 2026-11-20 18:20:00 → BOS 2026-11-20 21:53:00; nonstop; 153 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $290.00

• American Airlines AA469: ORD 2026-11-20 17:52:00 → BOS 2026-11-20 21:16:00; nonstop; 144 minutes. Local airport times.
• American Airlines AA1500: BOS 2026-11-23 12:12:00 → ORD 2026-11-23 14:22:00; nonstop; 190 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $300.00

• Delta Air Lines DL2570: ORD 2026-11-20 10:35:00 → BOS 2026-11-20 13:59:00; nonstop; 144 minutes. Local airport times.
• Delta Air Lines DL5606: BOS 2026-11-23 20:10:00 → ORD 2026-11-23 22:04:00; nonstop; 174 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $300.00

• United Airlines UA1896: ORD 2026-11-20 12:29:00 → BOS 2026-11-20 15:53:00; nonstop; 144 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-11-23 06:00:00 → ORD 2026-11-23 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $348.00

• American Airlines AA469: ORD 2026-11-27 17:52:00 → BOS 2026-11-27 21:16:00; nonstop; 144 minutes. Local airport times.
• American Airlines AA2015: BOS 2026-12-04 10:24:00 → ORD 2026-12-04 12:35:00; nonstop; 191 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $348.00

• American Airlines AA2089: ORD 2026-11-27 06:59:00 → BOS 2026-11-27 10:32:00; nonstop; 153 minutes. Local airport times.
• American Airlines AA2015: BOS 2026-12-04 10:24:00 → ORD 2026-12-04 12:35:00; nonstop; 191 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $360.00

• Delta Air Lines DL5855: ORD 2026-11-27 12:35:00 → BOS 2026-11-27 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2026-12-04 20:59:00 → ORD 2026-12-04 22:57:00; nonstop; 178 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $360.00

• United Airlines UA2320: ORD 2026-11-27 18:20:00 → BOS 2026-11-27 21:53:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA2496: BOS 2026-12-04 14:58:00 → ORD 2026-12-04 17:00:00; nonstop; 182 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $360.00

• Delta Air Lines DL2570: ORD 2026-11-27 10:35:00 → BOS 2026-11-27 13:59:00; nonstop; 144 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2026-12-04 20:59:00 → ORD 2026-12-04 22:57:00; nonstop; 178 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $360.00

• United Airlines UA1896: ORD 2026-11-27 12:29:00 → BOS 2026-11-27 15:53:00; nonstop; 144 minutes. Local airport times.
• United Airlines UA2496: BOS 2026-12-04 14:58:00 → ORD 2026-12-04 17:00:00; nonstop; 182 minutes. Local airport times.

2026-11-20 · one way · $145.00

• American Airlines AA3437 / AA4533: ORD 2026-11-20 08:00:00 → BOS 2026-11-20 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-11-20 08:00:00 → ROC 2026-11-20 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-11-20 12:50:00 → BOS 2026-11-20 14:17:00.

2026-11-20 · one way · $145.00

• American Airlines AA4780 / AA4026: ORD 2026-11-20 08:00:00 → BOS 2026-11-20 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-11-20 08:00:00 → BUF 2026-11-20 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-11-20 12:30:00 → BOS 2026-11-20 14:09:00.

2026-11-20 · one way · $145.00

• American Airlines AA2840 / AA1776: ORD 2026-11-20 15:19:00 → BOS 2026-11-20 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-11-20 15:19:00 → PHL 2026-11-20 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-11-20 19:55:00 → BOS 2026-11-20 21:19:00.

2026-11-20 · one way · $150.00

• Delta Air Lines DL2917 / DL5727: ORD 2026-11-20 10:06:00 → BOS 2026-11-20 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-11-20 10:06:00 → LGA 2026-11-20 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-11-20 15:00:00 → BOS 2026-11-20 16:25:00.

2026-11-20 · one way · $150.00

• United Airlines UA1128 / UA688: ORD 2026-11-20 13:00:00 → BOS 2026-11-20 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-11-20 13:00:00 → IAD 2026-11-20 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-11-20 17:15:00 → BOS 2026-11-20 18:57:00.

2026-11-20 → 2026-11-23 · $282.50

• American Airlines AA2840 / AA1776: ORD 2026-11-20 15:19:00 → BOS 2026-11-20 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-11-20 15:19:00 → PHL 2026-11-20 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-11-20 19:55:00 → BOS 2026-11-20 21:19:00.
• American Airlines AA1500: BOS 2026-11-23 12:12:00 → ORD 2026-11-23 14:22:00; nonstop; 190 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $282.50

• American Airlines AA3437 / AA4533: ORD 2026-11-20 08:00:00 → BOS 2026-11-20 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-11-20 08:00:00 → ROC 2026-11-20 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-11-20 12:50:00 → BOS 2026-11-20 14:17:00.
• American Airlines AA1500: BOS 2026-11-23 12:12:00 → ORD 2026-11-23 14:22:00; nonstop; 190 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $282.50

• American Airlines AA4780 / AA4026: ORD 2026-11-20 08:00:00 → BOS 2026-11-20 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-11-20 08:00:00 → BUF 2026-11-20 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-11-20 12:30:00 → BOS 2026-11-20 14:09:00.
• American Airlines AA1500: BOS 2026-11-23 12:12:00 → ORD 2026-11-23 14:22:00; nonstop; 190 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $292.50

• Delta Air Lines DL2917 / DL5727: ORD 2026-11-20 10:06:00 → BOS 2026-11-20 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-11-20 10:06:00 → LGA 2026-11-20 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-11-20 15:00:00 → BOS 2026-11-20 16:25:00.
• Delta Air Lines DL5606: BOS 2026-11-23 20:10:00 → ORD 2026-11-23 22:04:00; nonstop; 174 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $292.50

• United Airlines UA1128 / UA688: ORD 2026-11-20 13:00:00 → BOS 2026-11-20 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-11-20 13:00:00 → IAD 2026-11-20 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-11-20 17:15:00 → BOS 2026-11-20 18:57:00.
• United Airlines UA1414: BOS 2026-11-23 06:00:00 → ORD 2026-11-23 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $337.50

• American Airlines AA2840 / AA1776: ORD 2026-11-27 15:19:00 → BOS 2026-11-27 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-11-27 15:19:00 → PHL 2026-11-27 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-11-27 19:55:00 → BOS 2026-11-27 21:19:00.
• American Airlines AA2015: BOS 2026-12-04 10:24:00 → ORD 2026-12-04 12:35:00; nonstop; 191 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $337.50

• American Airlines AA3437 / AA4533: ORD 2026-11-27 08:00:00 → BOS 2026-11-27 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-11-27 08:00:00 → ROC 2026-11-27 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-11-27 12:50:00 → BOS 2026-11-27 14:17:00.
• American Airlines AA2015: BOS 2026-12-04 10:24:00 → ORD 2026-12-04 12:35:00; nonstop; 191 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $337.50

• American Airlines AA4780 / AA4026: ORD 2026-11-27 08:00:00 → BOS 2026-11-27 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-11-27 08:00:00 → BUF 2026-11-27 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-11-27 12:30:00 → BOS 2026-11-27 14:09:00.
• American Airlines AA2015: BOS 2026-12-04 10:24:00 → ORD 2026-12-04 12:35:00; nonstop; 191 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $349.50

• Delta Air Lines DL2917 / DL5727: ORD 2026-11-27 10:06:00 → BOS 2026-11-27 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-11-27 10:06:00 → LGA 2026-11-27 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-11-27 15:00:00 → BOS 2026-11-27 16:25:00.
• Delta Air Lines DL2804: BOS 2026-12-04 20:59:00 → ORD 2026-12-04 22:57:00; nonstop; 178 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $349.50

• United Airlines UA1128 / UA688: ORD 2026-11-27 13:00:00 → BOS 2026-11-27 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-11-27 13:00:00 → IAD 2026-11-27 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-11-27 17:15:00 → BOS 2026-11-27 18:57:00.
• United Airlines UA2496: BOS 2026-12-04 14:58:00 → ORD 2026-12-04 17:00:00; nonstop; 182 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $504.00

• Air Canada AC508 / AC772: ORD 2026-11-27 16:30:00 → BOS 2026-11-27 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-27 16:30:00 → YYZ 2026-11-27 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-27 20:55:00 → BOS 2026-11-27 22:37:00.
• Air Canada AC8695 / AC511: BOS 2026-12-04 15:10:00 → ORD 2026-12-04 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-12-04 15:10:00 → YYZ 2026-12-04 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-12-04 18:55:00 → ORD 2026-12-04 19:58:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

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New England for a week from other cities

Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Hotels in Boston with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Boston has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Boston: the 7 best neighborhoods, ranked · Boston hotels where a family of four can share one room

Hotels with an Axel review in Boston: Studio Allston Hotel · Holiday Inn Boston - Cambridge Area by IHG · The Bostonian Hotel Boston · YOTEL Boston · Cambria Hotel Boston Downtown - Seaport · All 117 reviewed hotels in Boston

For AI assistants

• This page: Flights from Chicago to New England for a week. Round-trip fares from Chicago to New England for a week: Boston, Burlington, Portland, Providence, Hartford and Manchester and more, for stays of 6 to 8 nights. The cheapest saved fare for each destination, and a link to search your own dates.
• Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.