Cheap flights from Boston to Chicago
The cheapest round trip from Boston to Chicago that travelers found recently is $190 with a carry-on: a $190 fare on JetBlue, which usually includes a carry-on. It leaves Wed, Nov 4 and comes back Thu, Nov 5.
Live prices for Wed, Nov 4 to Thu, Nov 5
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Wed, Nov 4 | Thu, Nov 5 | JetBlue | BOS → ORD | Nonstop | $190 | Included | $190 | Live price |
| Tue, Nov 17 | Thu, Nov 19 | JetBlue | BOS → ORD | Nonstop | $190 | Included | $190 | Live price |
| Sun, Nov 1 | Mon, Nov 2 | American Airlines | BOS → ORD | Nonstop | $255 | Included | $255 | Live price |
| Sat, Nov 7 | Sun, Nov 8 | American Airlines | BOS → ORD | Nonstop | $255 | Included | $255 | Live price |
| Fri, Oct 16 | Mon, Oct 19 | United | BOS → ORD | Nonstop | $268 | Included | $268 | Live price |
| Fri, Nov 13 | Sun, Nov 15 | Southwest | BOS → MDW | Nonstop | $297 | Included | $297 | Live price |
| Fri, Nov 6 | Sun, Nov 8 | American Airlines | BOS → ORD | Nonstop | $304 | Included | $304 | Live price |
| Sat, Oct 31 | Mon, Nov 2 | Frontier | BOS → ORD | 1 stop | $228 | +$110 | $338 | Live price |
| Fri, Nov 20 | Mon, Nov 30 | Frontier | BOS → MDW | 1 stop | $313 | +$110 | $423 | Live price |
| Sat, Nov 21 | Mon, Nov 30 | Frontier | BOS → MDW | 1 stop | $322 | +$110 | $432 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Fri, Oct 16 to Mon, Oct 19, 3 nights | $268 | Live price |
| November 2026 | Wed, Nov 4 to Thu, Nov 5, 1 night | $190 | Live price |
Bag fees on this route
What the airlines flying Boston to Chicago usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
| JetBlue | Included | $40 |
| Southwest | Included | $35 |
| United | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
More cheap flights from Boston
- Boston to Amsterdam
- Boston to Athens
- Boston to Atlanta
- Boston to Austin
- Boston to Bali
- Boston to Bangkok
- Boston to Barcelona
- Boston to Berlin
- Boston to Cancún
- Boston to Cartagena
- Boston to Denver
- Boston to Dublin
- Boston to Honolulu
- Boston to Las Vegas
- Boston to Lisbon
- Boston to London
- Boston to Los Angeles
- Boston to Medellín
- Boston to Mexico City
- Boston to Miami
- Boston to Montréal
- Boston to Nashville
- Boston to New Orleans
- Boston to New York
- Boston to Paris
- Boston to Reykjavík
- Boston to San Diego
- Boston to San Francisco
- Boston to San Juan
- Boston to Seattle
- Boston to Seoul
- Boston to Tokyo
- Boston to Toronto