Cheap flights from Boston to Chicago from $140 BOS → MDW, ORD, RFD
Logan International Airport (BOS) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD)
The cheapest one-way found recently is $140 with American Airlines, 24 Dec, found 5 days ago.
- Cheapest one-way found recently
- $140, American Airlines, found 5 days ago
- Cheapest month to fly
- November 2026, one-way fares from $119 found in the last 7 days
- Airlines with nonstop flights
- American Airlines, Southwest Airlines, jetBlue, United Airlines
- Shortest nonstop flight found
- 3 h
One-way
The cheapest one-way fare on each of 4 departure dates is usually $135 to $152.
Cheapest one-way found recently
$140
24 Dec · American Airlines
Logan International Airport (BOS) → O'Hare International Airport (ORD)
Leaves 6:00 a.m. · 5 h 8 min trip
1 stop · via Ronald Reagan National Airport (DCA)
found 5 days ago
Cheapest nonstop one-way
$149
28 Dec · Southwest Airlines
Logan International Airport (BOS) → Chicago Midway International Airport (MDW)
Leaves 10:25 p.m. · 3 h trip
nonstop
found 5 days ago
Found recently, and the cheapest we hold
$140 24 Decfound 5 days agoOpen this trip
$119 21 Novfound 7 days agoOpen this trip
What have prices looked like?
Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $88 to $149.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 4 departure dates from 21 Nov to 16 Mar 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 24 Dec to compare.
Every date we hold
35 fares on 4 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 21 Nov | $119 | Southwest Airlines | Logan International Airport (BOS) → Chicago Midway International Airport (MDW) | nonstop | found 7 days ago | Open this trip |
| 24 Dec | $140 | American Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 28 Dec | $143 | American Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | 1 stop | found 5 days ago | Open this trip |
| 16 Mar 2027 | $179 | American Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | nonstop | found 6 days ago | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from $119.
Airlines on the cheapest dates: American Airlines, Southwest Airlines.
Premium cabin fares from Boston to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 24 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Boston to Chicago?
One-way
Fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure.
From the cheapest one-way each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $198 | $114 | +108% | 16 |
| 7–13 days | $138 | $89 | +45% | 34 |
| 14–29 days | $95 | $88 | Cheapest seen | 39 |
| 30–59 days | $104 | $94 | +10% | 45 |
| 60–89 days | $106 | $99 | +12% | 25 |
| 90–179 days | $167 | $106 | +76% | 32 |
| 180+ days | $179 | $150 | +88% | 11 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Hartford → Chicago
142 km from Boston
$361
11 Jan 2027 – 15 Jan 2027 · BDL → ORD · out 1 stop, back nonstop
found 7 days ago
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
Hartford → Chicago
142 km from Boston
$150
$10 more than flying from Boston
19 Nov · BDL → ORD · nonstop
found 4 days ago
Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest one-way found recently is for 24 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a one-way flight from Boston to Chicago?
The cheapest one-way found recently is $140 with American Airlines, 24 Dec, found 5 days ago. The cheapest one-way we hold, of any age, is $119 with Southwest Airlines, 21 Nov, found 7 days ago. The cheapest one-way fare on each of 4 departure dates is usually $135 to $152.
What is the cheapest month to fly from Boston to Chicago?
November 2026 is the cheapest month for a one-way, from $119, 21 Nov, found 7 days ago.
How far ahead should I book a flight from Boston to Chicago?
In 49 days of prices between 24 Sept and 11 Nov, one-way fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure.
Is there a direct flight from Boston to Chicago?
Yes, the cheapest nonstop one-way found recently is $149 with Southwest Airlines, 28 Dec, found 5 days ago.
How long is the flight from Boston to Chicago?
The cheapest nonstop one-way found recently, with Southwest Airlines on 28 Dec, takes 3 h from Logan International Airport (BOS) to Chicago Midway International Airport (MDW). The cheapest one-way found recently, with American Airlines on 24 Dec, takes 5 h 8 min with 1 stop.
Which airlines have the cheapest flights from Boston to Chicago?
Between 21 Nov and 16 Mar 2027, American Airlines has the cheapest one-way on 3 of the 4 departure dates we hold, and Southwest Airlines on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work