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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 6/4. 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
ma 6/17
ma 6/24

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In the last 7 days travelers have searched 41,904,688 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 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

6/3ma
1 stopFrontier
8h 27mMDW-BOS
6/5ke
1 stopFrontier
6h 43mBOS-MDW
$118
5/30to
1 stopFrontier
24h 15mMDW-BOS
6/1la
1 stopFrontier
11h 10mBOS-MDW
$119
9/7la
1 stop
7h 26mSTL-BOS
9/11ke
1 stop
7h 27mBOS-STL
$148
6/1la
3 stopsSpirit Airlines
18h 09mORD-BOS
6/4ti
1 stopSpirit Airlines
12h 30mBOS-ORD
$154
6/9su
1 stopSpirit Airlines
11h 45mORD-BOS
6/12ke
nonstopSpirit Airlines
2h 54mBOS-ORD
$155
6/16su
1 stop
5h 44mORD-BOS
6/18ti
1 stop
12h 30mBOS-ORD
$160
5/31pe
nonstopJetBlue
2h 26mORD-BOS
6/4ti
nonstopJetBlue
2h 54mBOS-ORD
$177
5/31pe
nonstopJetBlue
2h 26mORD-BOS
6/1la
nonstopJetBlue
2h 55mBOS-ORD
$187
5/30to
nonstopAmerican Airlines
2h 20mORD-BOS
6/2su
nonstopAmerican Airlines
2h 52mBOS-ORD
$214
5/29ke
1 stopAmerican Airlines
4h 40mORD-BOS
6/2su
nonstopAmerican Airlines
2h 52mBOS-ORD
$222

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Recent one-way flight deals

6/4ti
1 stopSpirit Airlines
11h 01mORD-BOS
$33
7/9ti
nonstopSpirit Airlines
2h 28mORD-BOS
$34
6/4ti
1 stopFrontier
5h 12mORD-BOS
$50
5/29ke
1 stopFrontier
5h 07mORD-BOS
$54
5/31pe
nonstopUnited Airlines
2h 35mORD-BOS
$69
5/31pe
nonstopJetBlue
2h 26mORD-BOS
$89
10/10to
nonstopAmerican Airlines
2h 26mORD-BOS
$95
5/25la
nonstopJetBlue
2h 26mORD-BOS
$99
10/10to
1 stopUnited Airlines
5h 13mORD-BOS
$104
5/26su
1 stopAmerican Airlines
4h 44mORD-BOS
$128

Search by stops

Search by airline

Search by price

Last minute flights from Illinois to Boston

Last minute flight, train and bus deals

5/19su
multi-stopFrontier
24h 15mMDW-BOS
5/26su
multi-stopFrontier
8h 13mBOS-MDW
$174
5/19su
multi-stopFrontier
24h 15mMDW-BOS
5/29ke
multi-stopFrontier
11h 39mBOS-MDW
$199
5/23to
nonstopUnited Airlines
2h 35mORD-BOS
5/26su
nonstopUnited Airlines
2h 50mBOS-ORD
$208
5/23to
multi-stop
19h 54mORD-BOS
5/28ti
multi-stop
10h 08mBOS-ORD
$215
5/23to
nonstopUnited Airlines
2h 35mORD-BOS
5/26su
multi-stopUnited Airlines
4h 58mBOS-ORD
$218
5/19su
multi-stop
19h 54mORD-BOS
5/29ke
multi-stop
10h 08mBOS-ORD
$234
5/22ke
multi-stopSpirit Airlines
12h 46mORD-BOS
5/29ke
multi-stopSpirit Airlines
10h 08mBOS-ORD
$237
5/20ma
multi-stopSpirit Airlines
12h 59mORD-BOS
6/21pe
multi-stopSpirit Airlines
6h 05mBOS-ORD
$250
5/23to
nonstopAmerican Airlines
2h 15mORD-BOS
5/26su
nonstopAmerican Airlines
2h 57mBOS-ORD
$283
5/22ke
multi-stopAmerican Airlines
4h 44mORD-BOS
5/27ma
nonstopAmerican Airlines
3h 04mBOS-ORD
$291

Search by stops

Search by airline

Search by price