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Cheap flights Chicago — Boston

Chicago (MDW, US) Boston (BOS, US)
from $114 1 366 km ~2h 6m 16 flights found 3 airlines cheapest on Wednesday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $114 on 22.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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We
Th
Fr
Sa
Su
December 2026
Mo
Tu
We
Th
Fr
Sa
Su
January 2027
Mo
Tu
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Fr
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Prices found for 19 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
23 Dec 2026, Wed
Frontier Airlines F9 1458
05:35
MDW Chicago Midway International Airport
11:30
BOS Logan International Airport
5h 55m 1 stop
Clickavia
$114
View this ticket
23 Dec 2026, Wed
Southwest Airlines WN 2902
04:00
MDW Chicago Midway International Airport
06:25
BOS Logan International Airport
2h 25m Direct
Trip.com
$154
View this ticket
18 Nov 2026, Wed
Southwest Airlines WN 2900
22:15
MDW Chicago Midway International Airport
00:20
BOS Logan International Airport
2h 5m Direct
Farera
$204
View this ticket
19 Nov 2026, Thu
Southwest Airlines WN 2902
03:25
MDW Chicago Midway International Airport
05:45
BOS Logan International Airport
2h 20m Direct
Farera
$204
View this ticket
17 Nov 2026, Tue
Southwest Airlines WN 4113
17:30
MDW Chicago Midway International Airport
20:00
BOS Logan International Airport
2h 30m Direct
Farera
$205
View this ticket
01 Dec 2026, Tue
Southwest Airlines WN 3001
07:55
MDW Chicago Midway International Airport
17:30
BOS Logan International Airport
9h 35m 2 stops
Clickavia
$243
View this ticket
Route characteristics
Distance
1 366 km
Flight time
2h 6m
Time difference
+1h
Minimum price
from $114 (22.12.2026)
Average price
$250
Maximum price
$373
Departures per week
1
Cheapest day
Wednesday
Departure airports (1)
MDW Chicago Midway International Airport
Arrival airports (1)
BOS Logan International Airport
Airlines (3)
F9 Frontier Airlines G4 Allegiant Air WN Southwest Airlines
Agencies (4)
Clickavia Kiwi.com Trip.com Farera
Prices by day of week
Tuesday
$205
avg $224
Wednesday
$114
avg $157
Cheapest
Thursday
$204
avg $204
Price trend by month
November 2026
from $204
avg $204
3 flights
December 2026
from $114
avg $170
3 flights
Airlines — cheapest prices 3
Frontier Airlines
Frontier Airlines
Low-cost 1 flights · 1 days
$114
Allegiant Air
Allegiant Air
Low-cost 1 flights · 1 days
$150
Southwest Airlines
Southwest Airlines
Low-cost 14 flights · 12 days
$154
Where to buy tickets 4
Clickavia
3 tickets · 3 days
from $114
Kiwi.com
1 tickets · 1 days
from $150
Trip.com
5 tickets · 5 days
from $154
Farera
7 tickets · 6 days
from $159
Airports

From — Chicago (1)

  • MDW Chicago Midway International Airport

To — Boston (1)

  • BOS Logan International Airport
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Frequently asked questions about the route Chicago — Boston
How long is the flight from Chicago to Boston?
Approximate flight time — 2h 6m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Chicago to Boston?
The straight-line distance — 1 366 km.
How much do flights from Chicago to Boston cost?
The minimum price over 3 months — from $114 on 22.12.2026.
What is the average ticket price?
The average price — $250. Range: $114 — $373.
What is the time difference between Chicago and Boston?
The difference — +1h.
From which airports does Chicago operate flights?
From Chicago: MDW (Chicago Midway International Airport).
To which airports in Boston do flights arrive?
To Boston: BOS (Logan International Airport).
Which airlines fly this route?
This route is served by 3 airlines: Frontier Airlines, Allegiant Air, Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $154. Total direct flights found: 4.
Which day of the week is cheapest?
The cheapest day of the week — Wednesday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Chicago — Boston

Flights Chicago — Boston is a popular route. The straight-line distance is 1 366 km. Flight time 2h 6m. Time difference +1h.

From Chicago (MDW) flights depart from 1 airport: MDW. To Boston (BOS) — 1 arrival airport: BOS.

3 airlines operate on this route: Frontier Airlines, Allegiant Air, Southwest Airlines.

The minimum price for the next 3 months — from $114 (22.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $250, ranging from $114 to $373. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Wednesday.

Other destinations in United States from Chicago
Ontario
US
Providence
US
Pittsburgh
US
Phoenix
US
Philadelphia
US
Portland
US
Norfolk
US
Oakland
US

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