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Find cheap flights from Illinois to Boston from $30

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 7/23. 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
Fri 6/7
Fri 6/14

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In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

October

Cheapest flight

$30
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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

6/5Wed
nonstopSpirit Airlines
2h 29mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$50
6/5Wed
nonstopSpirit Airlines
2h 29mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$51
6/1Sat
1 stop
6h 08mORD-BOS
6/11Tue
nonstop
2h 54mBOS-ORD
$95
5/18Sat
1 stopFrontier
11h 35mMDW-BOS
5/22Wed
1 stopFrontier
6h 50mBOS-MDW
$101
6/1Sat
1 stop
6h 08mORD-BOS
6/10Mon
nonstop
2h 54mBOS-ORD
$107
5/18Sat
1 stopFrontier
11h 35mMDW-BOS
5/29Wed
1 stopFrontier
6h 50mBOS-MDW
$110
5/29Wed
nonstopJetBlue
2h 26mORD-BOS
6/4Tue
nonstopJetBlue
2h 54mBOS-ORD
$137
6/1Sat
nonstopAmerican Airlines
2h 17mORD-BOS
6/4Tue
nonstopAmerican Airlines
2h 56mBOS-ORD
$157
8/13Tue
nonstopJetBlue
2h 26mORD-BOS
8/24Sat
nonstopJetBlue
2h 54mBOS-ORD
$177
6/1Sat
nonstopAmerican Airlines
2h 17mORD-BOS
6/2Sun
nonstopAmerican Airlines
2h 58mBOS-ORD
$183

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Recent one-way flight deals

7/23Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$30
6/6Thu
nonstopSpirit Airlines
2h 28mORD-BOS
$31
5/22Wed
1 stopFrontier
5h 07mORD-BOS
$54
6/1Sat
1 stopFrontier
6h 08mORD-BOS
$55
5/29Wed
nonstopJetBlue
2h 26mORD-BOS
$69
5/25Sat
nonstopJetBlue
2h 26mORD-BOS
$95
6/10Mon
1 stopSun Country Air
13h 17mORD-BOS
$96
5/26Sun
nonstopUnited Airlines
2h 20mORD-BOS
$104
5/17Fri
nonstopUnited Airlines
2h 21mORD-BOS
$134
10/11Fri
1 stopSun Country Air
15h 30mORD-BOS
$141

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Last minute flights from Illinois to Boston

Last minute flight, train and bus deals

5/13Mon
multi-stopFrontier
15h 24mMDW-BOS
5/18Sat
multi-stopFrontier
22h 05mBOS-MDW
$143
5/13Mon
multi-stopFrontier
15h 24mMDW-BOS
5/18Sat
multi-stopFrontier
20h 25mBOS-MDW
$148
5/13Mon
nonstopUnited Airlines
2h 21mORD-BOS
5/18Sat
nonstopUnited Airlines
2h 53mBOS-ORD
$211
5/13Mon
nonstopJetBlue
2h 26mORD-BOS
5/18Sat
nonstopJetBlue
2h 54mBOS-ORD
$223
5/13Mon
multi-stopSpirit Airlines
20h 21mORD-BOS
5/14Tue
multi-stopSpirit Airlines
20h 36mBOS-ORD
$224
5/13Mon
multi-stopAmerican Airlines
5h 37mORD-BOS
5/16Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$227
5/13Mon
multi-stopSpirit Airlines
27h 33mORD-BOS
5/18Sat
multi-stopSpirit Airlines
14h 07mBOS-ORD
$235
5/13Mon
nonstopAmerican Airlines
2h 26mORD-BOS
5/16Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$243
5/12Sun
nonstopJetBlue
2h 29mORD-BOS
5/16Thu
nonstopJetBlue
2h 54mBOS-ORD
$329
5/12Sun
multi-stopUnited Airlines
5h 41mORD-BOS
5/14Tue
nonstopUnited Airlines
2h 48mBOS-ORD
$362

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Flights to Boston

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Illinois

Cabin classes:

$366
$534
$386
$131