Boston to Chicago BOS → MDW, ORD
Logan International Airport (BOS) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)
The cheapest return found recently is $314 with Southwest Airlines, 23 Dec – 1 Jan 2027, found 2 days ago. The cheapest one-way found recently is $123 with Frontier Airlines, 4 Nov, found yesterday.
Return
The cheapest return fare on each of 6 departure dates is usually $235 to $303.
Cheapest return found recently
$314
23 Dec – 1 Jan 2027 · Southwest Airlines
Logan International Airport (BOS) → Chicago Midway International Airport (MDW)
Leaves 10:25 p.m. · Return leaves 8:30 a.m. · 5 h 30 min of travel, both ways together
out nonstop, back nonstop
found 2 days ago
Cheapest nonstop return
$314
23 Dec – 1 Jan 2027 · Southwest Airlines
Logan International Airport (BOS) → Chicago Midway International Airport (MDW)
Leaves 10:25 p.m. · Return leaves 8:30 a.m. · 5 h 30 min of travel, both ways together
out nonstop, back nonstop
found 2 days ago
Found recently, and the cheapest we hold
$314 23 Dec – 1 Jan 2027found 2 days agoSee prices for these dates
$190 4 Nov – 5 Novfound 6 days agoSee prices for these dates
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $147 to $303.
At $314, the cheapest return found recently is above that range.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 6 departure dates from 31 Oct to 23 Dec, 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 9-night return fares leaving within 3 days of 23 Dec to compare.
Every date we hold
7 fares on 6 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 31 Oct – 2 Nov | $228 | Frontier Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 5 days ago | See prices for these dates |
| 1 Nov – 2 Nov | $255 | American Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| 4 Nov – 5 Nov | $190 | jetBlue | Logan International Airport (BOS) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| 5 Nov – 7 Nov | $306 | Frontier Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 3 days ago | See prices for these dates |
| 23 Nov – 28 Nov | $294 | Southwest Airlines | Logan International Airport (BOS) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| 23 Dec – 1 Jan 2027 | $314 | Southwest Airlines | Logan International Airport (BOS) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
Which month looks cheapest?
November 2026 is the cheapest month — from $190.
Airlines on the cheapest dates: Frontier Airlines, Southwest Airlines, American Airlines, jetBlue.
One-way
The cheapest one-way fare on each of 7 departure dates is usually $89 to $135.
Cheapest one-way found recently
$123
4 Nov · Frontier Airlines
Logan International Airport (BOS) → O'Hare International Airport (ORD)
Leaves 12:39 p.m. · 6 h 51 min trip
1 stop
found yesterday
Cheapest nonstop one-way
$171
26 Dec · United Airlines
Logan International Airport (BOS) → O'Hare International Airport (ORD)
Leaves 5:45 a.m. · 3 h 6 min trip
nonstop
found 3 days ago
Found recently, and the cheapest we hold
$123 4 Novfound yesterdayOpen this trip
$88 4 Novfound 5 days agoOpen this trip
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $88 to $113.
At $123, the cheapest one-way found recently is above that range.
25 days is a short history, so treat this range as an early guide.
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 7 departure dates from 28 Oct to 26 Dec, 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?
Yes. Among one-way fares leaving within 3 days of 4 Nov, 2 Nov costs $89: $34 less than the cheapest found recently.
jetBlue · Logan International Airport (BOS) → O'Hare International Airport (ORD) · nonstop · found 5 days ago
Every date we hold
8 fares on 7 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 28 Oct | $138 | Frontier Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | 1 stop | found yesterday | Open this trip |
| 31 Oct | $122 | Frontier Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | 1 stop | found 3 days ago | Open this trip |
| 2 Nov | $89 | jetBlue | Logan International Airport (BOS) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 3 Nov | $131 | Frontier Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | 1 stop | found yesterday | Open this trip |
| 4 Nov | $88 | jetBlue | Logan International Airport (BOS) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 9 Nov | $88 | jetBlue | Logan International Airport (BOS) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 26 Dec | $171 | United Airlines | Logan International Airport (BOS) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from $88.
Airlines on the cheapest dates: Frontier Airlines, jetBlue, United 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 23 Dec – 1 Jan 2027 in another cabin: Premium economy · Business · First
Today's prices for 4 Nov in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Boston to Chicago?
Return
Fares 14 to 29 days before departure were typically 42% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 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 | $375 | $251 | +74% | 21 |
| 7–13 days | $375 | $164 | +74% | 7 |
| 14–29 days | $216 | $190 | Cheapest seen | 15 |
| 30–59 days | $272 | $147 | +26% | 25 |
| 60–89 days | $332 | $250 | +54% | 14 |
| 90–179 days | $331 | $286 | +53% | 18 |
One-way
Fares 14 to 29 days before departure were typically 74% lower than 0 to 6 days before departure.
From the cheapest one-way each day between 24 Sept and 18 Oct (25 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 | $371 | $152 | +287% | 7 |
| 7–13 days | $154 | $113 | +60% | 20 |
| 14–29 days | $96 | $88 | Cheapest seen | 25 |
| 30–59 days | $99 | $94 | +3% | 25 |
| 60–89 days | $102 | $99 | +6% | 7 |
| 90–179 days | $165 | $154 | +72% | 18 |
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
$382
$68 more than flying from Boston
29 Oct – 5 Nov · BDL → ORD · out 1 stop, back 1 stop
found today
Providence → Chicago
66 km from Boston
$363
$49 more than flying from Boston
31 Oct – 2 Nov · PVD → RFD · out 2 stops, back 2 stops
found 6 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
$133
$10 more than flying from Boston
21 Nov · BDL → ORD · 1 stop
found 6 days ago
Providence → Chicago
66 km from Boston
$199
$76 more than flying from Boston
27 Oct · PVD → RFD · 2 stops
found 2 days ago
Manchester → Chicago
70 km from Boston
$351
$228 more than flying from Boston
26 Oct · MHT → ORD · 3 stops
found 3 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 return found recently is for 23 Dec – 1 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
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