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$32 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 8/27. 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
Thu 6/13
Thu 6/20

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In the last 7 days travelers have searched 42,566,405 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

July

Cheapest flight

$32
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 18% 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

6/5Wed
nonstopSpirit Airlines
2h 29mORD-BOS
6/8Sat
nonstopSpirit Airlines
2h 54mBOS-ORD
$62
9/11Wed
nonstopSpirit Airlines
2h 18mORD-BOS
9/18Wed
nonstopSpirit Airlines
2h 33mBOS-ORD
$63
6/1Sat
1 stopFrontier
6h 08mORD-BOS
6/5Wed
1 stopFrontier
16h 51mBOS-ORD
$99
5/29Wed
1 stopFrontier
5h 07mORD-BOS
6/1Sat
1 stopFrontier
14h 16mBOS-ORD
$100
5/29Wed
1 stop
5h 07mORD-BOS
5/31Fri
1 stop
12h 30mBOS-ORD
$107
5/30Thu
1 stop
5h 09mORD-BOS
6/4Tue
1 stop
6h 00mBOS-ORD
$117
5/31Fri
nonstopDelta
2h 36mORD-BOS
6/5Wed
nonstopDelta
2h 55mBOS-ORD
$137
6/1Sat
nonstopJetBlue
2h 26mORD-BOS
6/4Tue
nonstopJetBlue
2h 54mBOS-ORD
$163
5/25Sat
nonstopJetBlue
2h 26mORD-BOS
5/30Thu
nonstopJetBlue
2h 54mBOS-ORD
$167
5/29Wed
nonstopDelta
2h 27mORD-BOS
6/3Mon
nonstopDelta
2h 55mBOS-ORD
$189

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Recent one-way flight deals

8/27Tue
nonstopSpirit Airlines
2h 18mORD-BOS
$32
9/25Wed
nonstopSpirit Airlines
2h 18mORD-BOS
$38
5/29Wed
1 stopFrontier
5h 07mORD-BOS
$50
5/22Wed
1 stopFrontier
5h 07mORD-BOS
$52
5/30Thu
nonstopJetBlue
2h 29mORD-BOS
$69
8/17Sat
nonstopUnited Airlines
2h 22mORD-BOS
$79
8/17Sat
1 stopUnited Airlines
6h 23mORD-BOS
$88
8/15Thu
nonstopDelta
2h 12mORD-BOS
$95
5/25Sat
nonstopJetBlue
2h 26mORD-BOS
$99
5/24Fri
nonstopDelta
2h 36mORD-BOS
$134

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Search by price

Last minute flights from Illinois to Boston

Last minute flight, train and bus deals

5/18Sat
multi-stopFrontier
14h 47mORD-BOS
6/1Sat
multi-stopFrontier
14h 16mBOS-ORD
$136
5/18Sat
multi-stopFrontier
11h 35mMDW-BOS
6/1Sat
multi-stopFrontier
20h 12mBOS-MDW
$136
5/18Sat
multi-stop
14h 47mORD-BOS
5/26Sun
multi-stop
11h 25mBOS-ORD
$156
5/18Sat
multi-stop
14h 47mORD-BOS
5/22Wed
multi-stop
15h 39mBOS-ORD
$173
5/18Sat
nonstopDelta
2h 31mORD-BOS
5/26Sun
nonstopDelta
2h 59mBOS-ORD
$253
5/19Sun
multi-stopSpirit Airlines
11h 14mORD-BOS
5/29Wed
multi-stopSpirit Airlines
20h 39mBOS-ORD
$278
5/17Fri
nonstopDelta
2h 27mORD-BOS
5/27Mon
nonstopDelta
2h 55mBOS-ORD
$279
5/19Sun
multi-stopSpirit Airlines
11h 14mORD-BOS
5/28Tue
multi-stopSpirit Airlines
23h 37mBOS-ORD
$282
5/18Sat
nonstopAmerican Airlines
2h 28mORD-BOS
5/18Sat
multi-stopAmerican Airlines
5h 50mBOS-ORD
$285
5/18Sat
multi-stopAmerican Airlines
4h 40mORD-BOS
6/1Sat
nonstopAmerican Airlines
2h 58mBOS-ORD
$287

Search by stops

Search by airline

Search by price