Cheap flights from Chicago to Boston
The cheapest round trip from Chicago to Boston that travelers found recently is $229 with a carry-on: a $229 fare on JetBlue, which usually includes a carry-on. It leaves Thu, Oct 29 and comes back Sun, Nov 1.
Live prices for Thu, Oct 29 to Sun, Nov 1
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Thu, Oct 29 | Sun, Nov 1 | JetBlue | ORD → BOS | Nonstop | $229 | Included | $229 | Live price |
| Fri, Oct 23 | Tue, Oct 27 | JetBlue | ORD → BOS | Nonstop | $250 | Included | $250 | Live price |
| Mon, Dec 21 | Thu, Dec 24 | JetBlue | ORD → BOS | Nonstop | $264 | Included | $264 | Live price |
| Sat, Jan 2 | Tue, Jan 5 | United | ORD → BOS | Nonstop | $286 | Included | $286 | Live price |
| Fri, Oct 30 | Sun, Nov 1 | Allegiant | MDW → BOS | 1 stop | $308 | +$110 | $418 | Live price |
| Sun, Oct 25 | Tue, Oct 27 | Frontier | ORD → BOS | 1 stop | $323 | +$110 | $433 | Live price |
| Fri, Apr 16 | Sun, Apr 18 | American Airlines | ORD → BOS | Nonstop | $449 | Included | $449 | 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 | Thu, Oct 29 to Sun, Nov 1, 3 nights | $229 | Live price |
| December 2026 | Mon, Dec 21 to Thu, Dec 24, 3 nights | $264 | Live price |
| January 2027 | Sat, Jan 2 to Tue, Jan 5, 3 nights | $286 | Live price |
| April 2027 | Fri, Apr 16 to Sun, Apr 18, 2 nights | $449 | Live price |
Bag fees on this route
What the airlines flying Chicago to Boston 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 |
|---|---|---|
| Allegiant | $55 | $50 |
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
| JetBlue | Included | $40 |
| 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.
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