BOS → CHI
Cheap flights from Boston to Chicago
Compare fares from Boston to Chicago from airlines and travel agencies, then book directly with the seller.
BOS → CHI
FROM $91 · 1 STOP
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Boston to Chicago: what the fares show
Recent searches turned up one-way tickets from Boston to Chicago for as little as $91: Frontier Airlines, departing November 20, 2026, with one stop. Across the 4 months we track, November 2026 is the cheapest month to fly (from $91) and October 2026 the most expensive (from $134), a difference of $43. Non-stop fares appear in our data from $104, about $13 more than the cheapest connection. The non-stop flight takes about 2h 45m gate to gate. The low fares on this route come mostly from Frontier Airlines and Southwest Airlines.
Prices are in US dollars, one-way, economy, per adult, from searches made on Aviasales and checked . Fares change often; the price you pay is confirmed on the airline's or agency's site.
- Route
- BOS → CHI
- Lowest fare found
- $91 one-way
- Cheapest month
- November 2026
- Non-stop fares
- From $104
- Typical stops
- Non-stop
- Fastest itinerary
- 2h 45m
- Airlines in our data
- Frontier Airlines, Southwest Airlines
- Price range in our data
- $91 – $192
- Fares checked
Prices by date
| Date | Lowest fare |
|---|
Lowest fares found recently for each departure day. Live prices may differ.
Boston to Chicago fares by departure date
The 15 cheapest departure days in the fares we tracked for the coming weeks, one-way per adult, checked .
| Departure date | Day | From | Airline | Stops | Search |
|---|---|---|---|---|---|
| Mon | $161 | Frontier Airlines | 1 stop | Search October 26, 2026 | |
| Tue | $152 | Frontier Airlines | 1 stop | Search October 27, 2026 | |
| Thu | $155 | Frontier Airlines | 1 stop | Search October 29, 2026 | |
| Sat | $134 | Frontier Airlines | 1 stop | Search October 31, 2026 | |
| Sun | $192 | jetBlue | Non-stop | Search November 1, 2026 | |
| Mon | $167 | Frontier Airlines | 1 stop | Search November 2, 2026 | |
| Tue | $135 | Frontier Airlines | 1 stop | Search November 3, 2026 | |
| Wed | $135 | Frontier Airlines | 1 stop | Search November 4, 2026 | |
| Fri | $178 | Southwest Airlines | Non-stop | Search November 6, 2026 | |
| Sat | $117 | Frontier Airlines | 1 stop | Search November 7, 2026 | |
| Sun | $115 | American Airlines | Non-stop | Search November 15, 2026 | |
| Cheapest | Fri | $91 | Frontier Airlines | 1 stop | Search November 20, 2026 |
| Wed | $173 | Southwest Airlines | Non-stop | Search November 25, 2026 | |
| Tue | $104 | Southwest Airlines | Non-stop | Search December 22, 2026 | |
| Thu | $111 | jetBlue | Non-stop | Search December 24, 2026 |
Cheapest month to fly from Boston to Chicago
Lowest one-way economy fare per adult found for each departure month, checked October 26, 2026. Select a month to search that date.
| Month | Cheapest day | From | Airline | Stops | Search |
|---|---|---|---|---|---|
| October 2026 | $134 | Frontier Airlines | 1 stop | Search October 31, 2026 | |
| November 2026 Cheapest | $91 | Frontier Airlines | 1 stop | Search November 20, 2026 | |
| December 2026 | $104 | Southwest Airlines | Non-stop | Search December 22, 2026 | |
| January 2027 | $104 | Southwest Airlines | Non-stop | Search January 4, 2027 |
Planning the rest of the trip
Related routes
Boston to Chicago flights: FAQ
How much is a flight from Boston to Chicago?
The cheapest one-way fare we found recently is $91 (1 stop, departing November 20, 2026). Fares change with demand and the date you book, so run a search to see today's prices for your dates.
What is the cheapest month to fly from Boston to Chicago?
In our latest data, November 2026 has the lowest fares (from $91) and October 2026 the highest (from $134). The table above lists the lowest fare we found for each month.
Are there direct flights from Boston to Chicago?
Yes. Non-stop fares from Boston to Chicago appear in our recent data from $104. Schedules change, so check the live results for your dates.
Which airlines fly from Boston to Chicago?
The lowest fares we found on this route were sold by Frontier Airlines and Southwest Airlines. The live search covers more airlines and travel agencies than appear here.
How long does it take to fly from Boston to Chicago?
The quickest itinerary among the fares we tracked takes 2h 45m, including any connections. Cheaper fares often take longer because of layovers; each result shows its total travel time.
Does Flicket sell the tickets?
No. Flicket is a flight search site. We compare fares from airlines and travel agencies through our partner Aviasales, and you book directly with the airline or agency you choose, on their website and under their terms. Flicket adds no fee to the fare.
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