Find cheap flights from Illinois to Boston

BOS

Find cheap flights from Illinois to Boston

Round-trip
Economy
Washington (WAS)
Boston Logan Intl
Tue 8/11
Tue 8/18
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Boston

Good to know

Low season

September Best time to beat the crowds with an average 4% drop in price.

High season

December Most popular time to fly with an average 8% increase in price.

Average price of a round-trip

$243 (avg. price over the last 2 weeks)

Good deal for a round-trip

$101 or less

FAQs for booking Illinois to Boston flights

Which airlines have a flexible cancellation policy for flights from Illinois to Boston Logan Intl due to COVID-19?

Which airlines apply social distancing measures on flights from Illinois to Boston Logan Intl due to COVID-19?

How does KAYAK find such low prices on flights from Illinois to Boston?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Boston?

What is the Hacker Fare option on flights from Illinois to Boston?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Boston?

Top 5 airlines serving Illinois to Boston Logan Intl

Scores according to KAYAK customer reviews

8.2
JetBlue
Overall score based on 19,207 reviews
8.3
Boarding
8.3
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews
Read more about JetBlue

Book cheap flights from Illinois to Boston

Recent round-trip flight deals

8/13
Thu
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/17
Mon
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/21
Fri
nonstop
Major Airline
2h 26m
ORD - BOS
8/23
Sun
nonstop
Major Airline
2h 42m
BOS - ORD
7/29
Wed
nonstop
Spirit Airlines
2h 26m
ORD - BOS
7/31
Fri
nonstop
Spirit Airlines
2h 52m
BOS - ORD
8/7
Fri
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/9
Sun
nonstop
Spirit Airlines
2h 57m
BOS - ORD
7/31
Fri
nonstop
Spirit Airlines
2h 21m
ORD - BOS
8/6
Thu
nonstop
Spirit Airlines
2h 57m
BOS - ORD
9/8
Tue
1 stop
Delta
5h 15m
MDW - BOS
9/9
Wed
1 stop
Delta
4h 35m
BOS - MDW
9/19
Sat
nonstop
Spirit Airlines
2h 31m
ORD - BOS
9/26
Sat
nonstop
Spirit Airlines
2h 33m
BOS - ORD
7/29
Wed
nonstop
Spirit Airlines
2h 26m
ORD - BOS
7/29
Wed
1 stop
Spirit Airlines
14h 41m
BOS - ORD
8/13
Thu
1 stop
Spirit Airlines
4h 53m
ORD - BOS
8/17
Mon
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/7
Fri
1 stop
Spirit Airlines
9h 00m
ORD - BOS
8/9
Sun
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/29
Sat
1 stop
Spirit Airlines
9h 00m
ORD - BOS
9/5
Sat
nonstop
Spirit Airlines
2h 57m
BOS - ORD
8/4
Tue
1 stop
Spirit Airlines
12h 17m
ORD - BOS
8/10
Mon
nonstop
Spirit Airlines
2h 57m
BOS - ORD
Show more results

Recent one-way flight deals

7/29
Wed
nonstop
Spirit Airlines
2h 26m
ORD - BOS
7/29
Wed
nonstop
Major Airline
2h 25m
ORD - BOS
7/31
Fri
nonstop
Spirit Airlines
2h 21m
ORD - BOS
7/26
Sun
nonstop
Allegiant Air
2h 20m
ORD - BOS
8/12
Wed
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/10
Mon
1 stop
Cape Air
5h 22m
ORD - BOS
7/29
Wed
1 stop
Multiple Airlines
18h 11m
ORD - BOS
9/20
Sun
1 stop
Delta
5h 28m
MDW - BOS
7/26
Sun
1 stop
Spirit Airlines
4h 53m
ORD - BOS
9/7
Mon
nonstop
Spirit Airlines
2h 25m
ORD - BOS
8/15
Sat
nonstop
Spirit Airlines
2h 25m
ORD - BOS
7/23
Thu
1 stop
Delta
4h 02m
ORD - BOS
7/31
Fri
1 stop
Multiple Airlines
7h 04m
ORD - BOS
7/31
Fri
2 stops
Multiple Airlines
13h 38m
ORD - BOS
9/7
Mon
1 stop
Delta
5h 46m
ORD - BOS
7/29
Wed
1 stop
Major Airline
5h 55m
ORD - BOS
7/25
Sat
2 stops
Multiple Airlines
15h 13m
ORD - BOS
Show more results
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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