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$33 Find cheap flights from Illinois to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Boston departing on 7/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/22
Sat 6/29

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In the last 7 days travelers have searched 43,800,826 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

July

Cheapest flight

$33
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Illinois to Boston

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

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

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Illinois with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Illinois to Boston?

Find which airlines fly direct from Illinois to Logan Intl, which days they fly and book direct flights.

Nonstop departures

Illinois to Boston Logan Intl

Monday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Boston Logan Intl to Illinois

Monday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Book cheap flights from Illinois to Boston

Recent round-trip flight deals

9/11Wed
nonstopSpirit Airlines
2h 18mORD-BOS
9/16Mon
nonstopSpirit Airlines
2h 33mBOS-ORD
$51
6/11Tue
1 stopSpirit Airlines
10h 49mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$54
6/4Tue
1 stop
19h 28mORD-BOS
6/9Sun
nonstop
2h 54mBOS-ORD
$100
6/14Fri
nonstopJetBlue
2h 26mORD-BOS
6/17Mon
nonstopJetBlue
2h 54mBOS-ORD
$115
6/6Thu
nonstop
2h 28mORD-BOS
6/10Mon
1 stop
22h 52mBOS-ORD
$117
6/5Wed
nonstopJetBlue
2h 29mORD-BOS
6/16Sun
nonstopJetBlue
2h 54mBOS-ORD
$136
6/4Tue
1 stopFrontier
11h 32mSTL-BOS
7/6Sat
1 stopFrontier
6h 13mBOS-STL
$148
5/30Thu
1 stopFrontier
24h 15mMDW-BOS
6/1Sat
1 stopFrontier
7h 58mBOS-MDW
$156
6/2Sun
nonstopUnited Airlines
2h 20mORD-BOS
6/8Sat
1 stopUnited Airlines
5h 10mBOS-ORD
$170
7/19Fri
nonstopUnited Airlines
2h 35mORD-BOS
7/21Sun
nonstopUnited Airlines
2h 46mBOS-ORD
$198

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Recent one-way flight deals

7/9Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$33
6/12Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$34
6/20Thu
nonstopJetBlue
2h 26mORD-BOS
$58
5/29Wed
1 stopFrontier
5h 07mORD-BOS
$59
5/29Wed
1 stopFrontier
5h 07mORD-BOS
$61
6/21Fri
1 stopJetBlue
4h 40mORD-BOS
$67
6/17Mon
1 stopSun Country Air
13h 17mORD-BOS
$78
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$108
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$116
10/27Sun
1 stopSun Country Air
15h 20mSTL-BOS
$143

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Last minute flights from Illinois to Boston

Last minute flight, train and bus deals

5/28Tue
multi-stopSpirit Airlines
32h 22mORD-BOS
6/10Mon
nonstopSpirit Airlines
2h 54mBOS-ORD
$123
5/26Sun
multi-stop
4h 57mORD-BOS
6/12Wed
nonstop
2h 54mBOS-ORD
$127
5/28Tue
nonstopDelta
2h 29mORD-BOS
6/11Tue
nonstopDelta
2h 57mBOS-ORD
$157
5/28Tue
multi-stopJetBlue
5h 49mORD-BOS
6/11Tue
nonstopJetBlue
2h 54mBOS-ORD
$176
5/26Sun
multi-stopFrontier
4h 57mORD-BOS
5/31Fri
multi-stopFrontier
16h 04mBOS-ORD
$179
5/26Sun
multi-stopFrontier
4h 57mORD-BOS
5/30Thu
multi-stopFrontier
16h 38mBOS-ORD
$180
5/28Tue
nonstopJetBlue
2h 26mORD-BOS
6/12Wed
nonstopJetBlue
2h 54mBOS-ORD
$191
5/28Tue
multi-stopAmerican Airlines
4h 40mORD-BOS
5/29Wed
nonstopAmerican Airlines
2h 57mBOS-ORD
$225
5/24Fri
nonstopDelta
2h 36mORD-BOS
6/11Tue
nonstopDelta
2h 51mBOS-ORD
$227
5/25Sat
multi-stopAmerican Airlines
5h 16mORD-BOS
6/11Tue
nonstopAmerican Airlines
2h 55mBOS-ORD
$234

Search by stops

Search by airline

Search by price