Chicago (ORD) to Boston (BOS) · Dec 16, 2026 · choose your return date

Chicago (ORD) to Boston (BOS): round-trip and one-way prices for 1 departure dates, Dec 16, 2026–Dec 16, 2026. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

JetBlue, nonstop, from $262 round trip · United, nonstop, from $271 round trip

Ticketing airlines with departures in this calendar: American Airlines, JetBlue Airways, United Airlines.

Saved nonstop flight times: 2h 26m–2h 28m outbound; 3h 6m–3h 13m returning.

How to read the calendar: published Axel-exclusive USD totals for one adult, including required taxes; basic economy may apply. Each return range includes its own prices. Only the listed dates and options are priced. Date links open published details; live search checks availability and lets you select flights.

To open an exact round trip, append /mon-d for the return to the departure URL (for example /dec-13), or /one-way for a one-way trip.

Hotels: under a departure date, hotels in Boston link to each hotel's page for that arrival date, where every stay length is priced for 2 adults in 1 room. When a price is shown, it is the nightly rate over the first 3 nights, from the lowest saved total among the shortlisted hotels in that star tier.

Chicago to Boston flight prices by month

December 2026: Dec 16 from $262.

Month summaries show the lowest displayed round-trip total for each departure. Match your return date to the calendar below.

Chicago to Boston flights in December 2026: price by departure date

ORD → BOS · USD · 1 adult · economy · published Nov 12, 2026

Wed, Dec 16, 2026 | return Dec 17, Dec 18–19, Dec 20–22, Dec 23, Dec 24, Dec 25, Dec 29, Dec 30, Dec 31 · JetBlue $262 | return Dec 26, Dec 27–28 · JetBlue $304 | return Jan 1–2, 2027, Jan 3, 2027, Jan 4, 2027, Jan 5–6, 2027, Jan 7–12, 2027, Jan 13, 2027, Jan 14, 2027, Jan 15, 2027, Jan 16–17, 2027, Jan 18–20, 2027, Jan 21–22, 2027, Jan 23–24, 2027, Jan 25, 2027, Jan 26–28, 2027, Jan 29, 2027, Jan 30, 2027, Jan 31–Feb 4, 2027, Feb 5, 2027, Feb 6, 2027, Feb 7–8, 2027, Feb 9, 2027, Feb 10, 2027, Feb 11–13, 2027, Feb 14–15, 2027, Feb 16, 2027, Feb 17, 2027, Feb 18, 2027, Feb 19, 2027, Feb 22–23, 2027, Feb 24, 2027, Feb 25, 2027, Feb 26–28, 2027, Mar 1, 2027, Mar 2, 2027, Mar 3–4, 2027, Mar 5–7, 2027, Mar 8, 2027, Mar 9–10, 2027, Mar 11–12, 2027, Mar 13–16, 2027 · JetBlue $293 | return Feb 20, 2027, Feb 21, 2027 · JetBlue $325 | one-way · American $136 | Dec 17 · Dec 18 · Dec 19 · Dec 20 · Dec 21 · Dec 22 · Dec 23 · Dec 24 · Dec 25 · Dec 26 · Dec 27 · Dec 28 · Dec 29 · Dec 30 · Dec 31 · Jan 1 · Jan 2 · Jan 3 · Jan 4 · Jan 5 · Jan 6 · Jan 7 · Jan 8 · Jan 9 · Jan 10 · Jan 11 · Jan 12 · Jan 13 · Jan 14 · Jan 15 · Jan 16 · Jan 17 · Jan 18 · Jan 19 · Jan 20 · Jan 21 · Jan 22 · Jan 23 · Jan 24 · Jan 25 · Jan 26 · Jan 27 · Jan 28 · Jan 29 · Jan 30 · Jan 31 · Feb 1 · Feb 2 · Feb 3 · Feb 4 · Feb 5 · Feb 6 · Feb 7 · Feb 8 · Feb 9 · Feb 10 · Feb 11 · Feb 12 · Feb 13 · Feb 14 · Feb 15 · Feb 16 · Feb 17 · Feb 18 · Feb 19 · Feb 20 · Feb 21 · Feb 22 · Feb 23 · Feb 24 · Feb 25 · Feb 26 · Feb 27 · Feb 28 · Mar 1 · Mar 2 · Mar 3 · Mar 4 · Mar 5 · Mar 6 · Mar 7 · Mar 8 · Mar 9 · Mar 10 · Mar 11 · Mar 12 · Mar 13 · Mar 14 · Mar 15 · Mar 16
Hotels in Boston from Dec 16, 2026 (per night, 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $107 a night · 4★ Hyatt Regency Boston/Cambridge, $140 a night · 5★ Omni Boston Hotel at the Seaport, $283 a night

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Dec 16, 2026 · choose your return date: 1 adult in economy, no fare priced at the moment. 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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: no fare is priced here right now. Choose travelers and dates and enter the traveler's own trip there for live prices.
• 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.

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