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$30 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 6/27. 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 6/27
Thu 7/4

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In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

June

Cheapest flight

$30
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 19% 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

6/11Tue
1 stopFrontier
7h 42mMDW-BOS
6/12Wed
1 stopFrontier
25h 15mBOS-MDW
$127
8/20Tue
1 stopFrontier
10h 26mMDW-BOS
8/28Wed
1 stopFrontier
13h 39mBOS-MDW
$133
7/11Thu
nonstopSpirit Airlines
2h 28mORD-BOS
7/15Mon
nonstopSpirit Airlines
2h 54mBOS-ORD
$146
6/13Thu
1 stopSpirit Airlines
9h 37mORD-BOS
6/17Mon
1 stopSpirit Airlines
11h 21mBOS-ORD
$147
6/11Tue
1 stop
6h 45mSTL-BOS
7/6Sat
1 stop
6h 13mBOS-STL
$147
6/11Tue
nonstopAmerican Airlines
2h 26mORD-BOS
6/12Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
$157
6/4Tue
nonstopJetBlue
2h 26mORD-BOS
6/11Tue
nonstopJetBlue
2h 54mBOS-ORD
$160
6/4Tue
nonstopJetBlue
2h 26mORD-BOS
6/8Sat
nonstopJetBlue
2h 53mBOS-ORD
$163
6/4Tue
nonstopAmerican Airlines
2h 26mORD-BOS
6/9Sun
nonstopAmerican Airlines
2h 55mBOS-ORD
$170
6/30Sun
1 stop
11h 14mORD-BOS
7/4Thu
1 stop
8h 46mBOS-ORD
$175

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Recent one-way flight deals

6/27Thu
nonstopSpirit Airlines
2h 28mORD-BOS
$30
7/17Wed
nonstopSpirit Airlines
2h 28mORD-BOS
$31
6/4Tue
1 stopFrontier
5h 12mORD-BOS
$58
8/28Wed
1 stopFrontier
10h 26mMDW-BOS
$64
6/20Thu
1 stopJetBlue
4h 40mORD-BOS
$67
6/11Tue
nonstopUnited Airlines
2h 31mORD-BOS
$79
6/4Tue
nonstopJetBlue
2h 26mORD-BOS
$82
6/12Wed
2 stops
10h 16mSTL-BOS
$84
7/1Mon
2 stops
11h 23mSTL-BOS
$96
6/3Mon
nonstopUnited Airlines
2h 35mORD-BOS
$107

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Last minute flights from Illinois to Boston

Last minute flight, train and bus deals

5/30Thu
multi-stop
5h 09mORD-BOS
6/4Tue
multi-stop
10h 17mBOS-ORD
$129
6/2Sun
multi-stop
19h 54mORD-BOS
6/5Wed
multi-stop
12h 30mBOS-ORD
$133
5/29Wed
multi-stopFrontier
5h 07mORD-BOS
6/1Sat
multi-stopFrontier
14h 16mBOS-ORD
$180
5/29Wed
multi-stopFrontier
5h 07mORD-BOS
6/3Mon
multi-stopFrontier
16h 12mBOS-ORD
$181
6/2Sun
multi-stopSpirit Airlines
11h 14mORD-BOS
6/5Wed
multi-stopSpirit Airlines
12h 38mBOS-ORD
$186
6/2Sun
multi-stopSpirit Airlines
11h 14mORD-BOS
6/12Wed
nonstopSpirit Airlines
2h 54mBOS-ORD
$187
6/1Sat
multi-stopAmerican Airlines
5h 16mORD-BOS
7/3Wed
nonstopAmerican Airlines
2h 55mBOS-ORD
$245
5/31Fri
nonstopAmerican Airlines
2h 15mORD-BOS
6/10Mon
nonstopAmerican Airlines
2h 55mBOS-ORD
$247
5/31Fri
nonstopJetBlue
2h 26mORD-BOS
6/3Mon
nonstopJetBlue
2h 54mBOS-ORD
$250
5/30Thu
multi-stopJetBlue
5h 54mORD-BOS
6/3Mon
nonstopJetBlue
2h 54mBOS-ORD
$259

Search by stops

Search by airline

Search by price