Chicago (ORD) to Boston (BOS) · Feb 24, 2027 · choose your return date

Chicago (ORD) to Boston (BOS): round-trip and one-way prices for 1 departure dates, Feb 24, 2027–Feb 24, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

JetBlue, nonstop, from $324 round trip · American, nonstop, from $335 round trip

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

Saved nonstop flight times: 2h 22m–2h 28m outbound; 2h 57m–3h 4m 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

February 2027: Feb 24 from $324.

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 February 2027: price by departure date

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

Wed, Feb 24, 2027 | return Feb 25, Feb 26–Mar 1, Mar 2–3, Mar 4–6, Mar 7–8, Mar 9, Mar 10–13, Mar 14, Mar 15–18, Mar 22–23, Mar 24–26, Mar 27 · JetBlue $324 | return Mar 19, Mar 20, Mar 21 · JetBlue $368 | return Mar 28–29, Apr 1–2, Apr 5–9, Apr 11, Apr 13–15, Apr 19–21, Apr 27–29, May 1–2, May 6, May 9–10, May 13–15, May 17–20, May 22–25 · United $335 | return Mar 30–31, Apr 3–4, Apr 10, Apr 12, Apr 16–18, Apr 22, Apr 30, May 3–5, May 7–8, May 11–12, May 16, May 21 · American $335 | return Apr 23–24 · American $407 | return Apr 25–26 · United $407 | one-way · American $167 | 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 · Mar 17 · Mar 18 · Mar 19 · Mar 20 · Mar 21 · Mar 22 · Mar 23 · Mar 24 · Mar 25 · Mar 26 · Mar 27 · Mar 28 · Mar 29 · Mar 30 · Mar 31 · Apr 1 · Apr 2 · Apr 3 · Apr 4 · Apr 5 · Apr 6 · Apr 7 · Apr 8 · Apr 9 · Apr 10 · Apr 11 · Apr 12 · Apr 13 · Apr 14 · Apr 15 · Apr 16 · Apr 17 · Apr 18 · Apr 19 · Apr 20 · Apr 21 · Apr 22 · Apr 23 · Apr 24 · Apr 25 · Apr 26 · Apr 27 · Apr 28 · Apr 29 · Apr 30 · May 1 · May 2 · May 3 · May 4 · May 5 · May 6 · May 7 · May 8 · May 9 · May 10 · May 11 · May 12 · May 13 · May 14 · May 15 · May 16 · May 17 · May 18 · May 19 · May 20 · May 21 · May 22 · May 23 · May 24 · May 25
Hotels in Boston from Feb 24, 2027 (per night, 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $136 a night · 4★ The Bostonian Hotel Boston, $172 a night · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $365 a night

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Feb 24, 2027 · 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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