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$52 Find cheap flights from Massachusetts to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 6/11. 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
Sun 6/30
Sun 7/7

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In the last 7 days travelers have searched 42,787,818 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

May

Cheapest flight

$52
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Boston to Chicago O'Hare Airport

FAQs for booking flights from Massachusetts to Chicago

  • How does KAYAK find such low prices on flights from Massachusetts to Chicago?

    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 Massachusetts to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Massachusetts 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 Massachusetts to Chicago?

    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 Chicago with an airline and back to Massachusetts with another airline.

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

    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 Chicago from Massachusetts 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 Massachusetts to Chicago?

Find which airlines fly direct from Massachusetts to Chicago, which days they fly and book direct flights.

Nonstop departures

Massachusetts to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights

Nonstop returns

Chicago to Massachusetts

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights
See more direct flights

Book cheap flights from Massachusetts to Chicago

Recent round-trip flight deals

6/11Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
6/12Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$52
6/11Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
6/12Wed
1 stopSpirit Airlines
12h 02mORD-BOS
$53
6/10Mon
1 stop
16h 52mBOS-ORD
6/11Tue
nonstop
2h 28mORD-BOS
$89
6/10Mon
1 stop
16h 52mBOS-ORD
6/18Tue
nonstop
2h 28mORD-BOS
$100
8/15Thu
1 stopFrontier
7h 37mBOS-MDW
8/20Tue
1 stopFrontier
10h 26mMDW-BOS
$136
6/11Tue
1 stopFrontier
6h 12mBDL-ORD
6/18Tue
1 stopFrontier
9h 14mORD-BDL
$137
6/17Mon
nonstopJetBlue
2h 57mBOS-ORD
8/27Tue
nonstopJetBlue
2h 26mORD-BOS
$147
8/17Sat
1 stopJetBlue
5h 11mBOS-ORD
8/20Tue
nonstopJetBlue
2h 26mORD-BOS
$156
8/17Sat
nonstopAmerican Airlines
2h 53mBOS-ORD
8/19Mon
nonstopAmerican Airlines
2h 31mORD-BOS
$157
11/9Sat
nonstopAmerican Airlines
3h 00mBOS-ORD
11/12Tue
nonstopAmerican Airlines
2h 19mORD-BOS
$189

Search by stops

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Recent one-way flight deals

9/11Wed
1 stopSpirit Airlines
11h 10mBDL-ORD
$53
6/11Tue
1 stopFrontier
6h 12mBDL-ORD
$58
6/14Fri
nonstopDelta
2h 57mBOS-ORD
$79
7/4Thu
nonstopUnited Airlines
2h 46mBOS-ORD
$80
6/17Mon
nonstopDelta
2h 57mBOS-ORD
$83
6/12Wed
1 stop
18h 51mBOS-RFD
$85
6/13Thu
1 stopJetBlue
4h 45mBOS-ORD
$88
6/26Wed
1 stop
18h 51mBOS-RFD
$89
6/6Thu
1 stopJetBlue
7h 38mBOS-ORD
$91
6/9Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$117

Search by stops

Search by airline

Search by price

Last minute flights from Massachusetts to Chicago

Last minute flight, train and bus deals

6/5Wed
multi-stop
16h 51mBOS-ORD
7/11Thu
nonstop
2h 26mORD-BOS
$100
6/5Wed
multi-stopFrontier
14h 40mBOS-MDW
6/11Tue
multi-stopFrontier
7h 42mMDW-BOS
$115
6/5Wed
multi-stop
16h 51mBOS-ORD
7/11Thu
multi-stop
11h 29mORD-BOS
$121
6/5Wed
multi-stopSpirit Airlines
17h 15mBOS-ORD
6/11Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$142
6/5Wed
multi-stopFrontier
6h 43mBOS-MDW
7/11Thu
multi-stopFrontier
10h 22mMDW-BOS
$154
6/4Tue
multi-stopSpirit Airlines
23h 15mBOS-ORD
6/8Sat
nonstopSpirit Airlines
2h 29mORD-BOS
$160
6/5Wed
nonstopJetBlue
2h 55mBOS-ORD
7/11Thu
nonstopJetBlue
2h 26mORD-BOS
$170
6/3Mon
nonstopJetBlue
2h 55mBOS-ORD
6/15Sat
nonstopJetBlue
2h 26mORD-BOS
$247
6/3Mon
nonstopAmerican Airlines
2h 56mBOS-ORD
6/13Thu
nonstopAmerican Airlines
2h 25mORD-BOS
$255
6/3Mon
nonstopAmerican Airlines
3h 04mBOS-ORD
6/16Sun
nonstopAmerican Airlines
2h 25mORD-BOS
$257

Search by stops

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Search by price

Flights to Chicago

Return flight deals:

Chicago - Massachusetts

Cabin classes:

$419
$555
$234
$124