Chicago to Boston MDW, ORD, RFD → BOS
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Logan International Airport (BOS)
The cheapest return found recently is $323 with Frontier Airlines, 25 Oct – 27 Oct, found 5 days ago. The cheapest one-way found recently is $731 with Allegiant Air, 28 Nov, found yesterday.
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$323
25 Oct – 27 Oct · Frontier Airlines
O'Hare International Airport (ORD) → Logan International Airport (BOS)
Leaves 6:58 p.m. · Return leaves 11:12 a.m. · 23 h 37 min of travel, both ways together
out 1 stop, back 1 stop
found 5 days ago
Cheapest nonstop return
$368
25 Oct – 27 Oct · Southwest Airlines
Chicago Midway International Airport (MDW) → Logan International Airport (BOS)
Leaves 7:50 a.m. · Return leaves 5:55 p.m. · 4 h 55 min of travel, both ways together
out nonstop, back nonstop
found 5 days ago
Found recently, and the cheapest we hold
$323 25 Oct – 27 Octfound 5 days agoSee prices for these dates
$308 30 Oct – 1 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 $204 to $323.
At $323, the cheapest return found recently is at the high end of 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?
Not enough comparable prices yet: we hold return fares on 2 departure dates and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 2-night return fares leaving within 3 days of 25 Oct to compare.
Every date we hold
7 fares on 2 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 25 Oct – 27 Oct | $323 | Frontier Airlines | O'Hare International Airport (ORD) → Logan International Airport (BOS) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 30 Oct – 1 Nov | $308 | Allegiant Air | Chicago Midway International Airport (MDW) → Logan International Airport (BOS) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
Airlines on the cheapest dates: Frontier Airlines, Allegiant Air.
One-way
The cheapest one-way fare on each of 4 departure dates is usually $95 to $392.
Cheapest one-way found recently
$731
28 Nov · Allegiant Air
Chicago Rockford International Airport (RFD) → Logan International Airport (BOS)
Leaves 8:50 a.m. · 12 h 4 min trip
1 stop
found yesterday
Cheapest nonstop one-way
$88
4 Nov · jetBlue
O'Hare International Airport (ORD) → Logan International Airport (BOS)
Leaves 1:00 p.m. · 2 h 48 min trip
nonstop
found 5 days ago
Found recently, and the cheapest we hold
$731 28 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 $86 to $157.
At $731, 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 4 departure dates from 4 Nov to 29 Nov, 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 28 Nov, 29 Nov costs $319: $412 less than the cheapest found recently.
United Airlines · O'Hare International Airport (ORD) → Logan International Airport (BOS) · nonstop · found 5 days ago
Every date we hold
9 fares on 4 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 4 Nov | $88 | jetBlue | O'Hare International Airport (ORD) → Logan International Airport (BOS) | nonstop | found 5 days ago | Open this trip |
| 14 Nov | $97 | Southwest Airlines | Chicago Midway International Airport (MDW) → Logan International Airport (BOS) | nonstop | found 5 days ago | Open this trip |
| 28 Nov | $612 | Allegiant Air | Chicago Rockford International Airport (RFD) → Logan International Airport (BOS) | 2 stops | found 6 days ago | Open this trip |
| 29 Nov | $319 | United Airlines | O'Hare International Airport (ORD) → Logan International Airport (BOS) | nonstop | found 5 days ago | Open this trip |
Airlines on the cheapest dates: jetBlue, Southwest Airlines, Allegiant Air, United Airlines.
Premium cabin fares from Chicago to Boston
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 25 Oct – 27 Oct in another cabin: Premium economy · Business · First
Today's prices for 28 Nov in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Boston?
Return
Fares 14 to 29 days before departure were typically 43% 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 | $369 | $369 | +77% | 11 |
| 7–13 days | $299 | $234 | +43% | 15 |
| 14–29 days | $209 | $209 | Cheapest seen | 13 |
| 30–59 days | $262 | $204 | +25% | 16 |
| 60–89 days | $264 | $264 | +26% | 8 |
| 180+ days | $312 | $312 | +49% | 15 |
One-way
Fares 14 to 29 days before departure were typically 15% lower than 7 to 13 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 |
|---|---|---|---|---|
| 7–13 days | $119 | $108 | +18% | 8 |
| 14–29 days | $101 | $86 | Cheapest seen | 18 |
| 30–59 days | $118 | $90 | +17% | 21 |
| 180+ days | $163 | $157 | +61% | 16 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
One-way
Chicago → Manchester
70 km from Boston
$211
$520 less than flying to Boston
16 Nov · MDW → MHT · stops unknown
found 3 days ago
South Bend → Boston
116 km from Chicago
$323
$408 less than flying from Chicago
26 Oct · SBN → BOS · 2 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 25 Oct – 27 Oct. 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