Chicago to Boston (BOS) flight deals
Chicago to Boston (BOS) from $309 round trip, Dec 16 to 19, 2026 (airline price $327), seen Oct 17.
For live prices on exact dates, each month below opens a day-by-day date picker; no account needed.
Compare Chicago to Boston (BOS) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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Fare examples by month
One-way and round-trip totals, shown separately · Economy · USD, saved from earlier searches. Each month opens its day-by-day date picker for live prices.
| Month | Trip type | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|---|
| October 2026 | Round trip | 1 adult · 3 days | $378–$397 | $399–$418 |
| November 2026 | One way | 1 adult | $101 | $107 |
| November 2026 | Round trip | 1 adult · 2–5 days | $398–$588 | $419–$621 |
| December 2026 | Round trip | 1 adult · 3 days | $309 | $327 |
Flights from Chicago · Chicago to United States flight deals
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Fares observed October 17 – 20, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
October 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Oct 26–29, 2026 · 3 days | Out: United Airlines 1186 · Nonstop · 2h 18m · 06:00–09:18 local; Return: Frontier Airlines 3511 / 1595 · 1 stop (ATL) · 7h 6m · 12:39–18:45 local | $378 · Save $21 | $399 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Oct 26–29, 2026 · 3 days | Out: United Airlines 1186 · Nonstop · 2h 18m · 06:00–09:18 local; Return: Delta Air Lines 2804 · Nonstop · 2h 51m · 19:40–21:31 local | $397 · Save $21 | $418 | Customer link — Open these flights in Axel · Optional: check axel prices |
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November 2026
1 adult · Economy · One-way totals
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| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 18, 2026 | Out: United Airlines 2213 · Nonstop · 2h 19m · 07:00–10:19 local | $101 · Save $6 | $107 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Nov 22–24, 2026 · 2 days | Out: Southwest Airlines 2900 · Nonstop · 2h 10m · 13:00–16:10 local; Return: Southwest Airlines 819 / 2651 · 1 stop (STL) · 7h 40m · 05:35–12:15 local | $398 · Save $21 | $419 | Customer link — Open these flights in Axel · Optional: check axel prices |
| MDW | Nov 22–24, 2026 · 2 days | Out: Southwest Airlines 2900 · Nonstop · 2h 10m · 13:00–16:10 local; Return: Southwest Airlines 4999 · Nonstop · 2h 45m · 07:00–08:45 local | $408 · Save $21 | $429 | Customer link — Open these flights in Axel · Optional: check axel prices |
| MDW | Nov 24–29, 2026 · 5 days | Out: Southwest Airlines 2900 · Nonstop · 2h 15m · 13:05–16:20 local; Return: Southwest Airlines 816 · Nonstop · 2h 45m · 20:00–21:45 local | $588 · Save $33 | $621 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 16–19, 2026 · 3 days | Out: United Airlines 1896 · Nonstop · 2h 24m · 12:29–15:53 local; Return: United Airlines 1414 · Nonstop · 3h 6m · 05:45–07:51 local | $309 · Save $18 | $327 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 15–19, 2026 · 4 days | Out: United Airlines 1606 · Nonstop · 2h 26m · 10:28–13:54 local | From $269 · Save $15 | From $284 | Check Axel prices |
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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
For AI assistants
- This page: Chicago to Boston (BOS) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- 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.