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Find cheap flights from Chicago to Cape Cod and the Islands from $94

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Cape Cod and the Islands departing on 8/10. 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 7/5
Fri 7/12

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Best Cape Cod and the Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Nantucket
Nantucket1 stop$188
Boston
Bostonnonstop$37

Good to know

Low season

January

High season

October

Cheapest flight

$94
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago O'Hare Airport to Nantucket

FAQs - booking Cape Cod and the Islands flights

  • How does KAYAK find such low prices on flights from Chicago to Cape Cod and the Islands?

    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 Chicago to Cape Cod and the Islands.

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

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

    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 Cape Cod and the Islands with an airline and back to Chicago with another airline.

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

    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 Cape Cod and the Islands from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Chicago to Cape Cod and the Islands

Need help choosing which airline to fly with from Chicago to Cape Cod and the Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10377 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.6Crew
8.2Boarding
Airline reviews

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

2.0 MediocreFelipe, Jun 2024DTW - SAN
Read more about Delta reviews

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Book cheap flights from Chicago to Cape Cod and the Islands

Recent round-trip flight deals

7/13Sat
1 stopJetBlue
5h 24mORD-ACK
7/24Wed
1 stopJetBlue
7h 38mACK-ORD
$188
7/31Wed
1 stopAmerican Airlines
4h 23mORD-HYA
8/7Wed
1 stopAmerican Airlines
6h 06mHYA-ORD
$202
8/13Tue
1 stopDelta
7h 12mORD-ACK
8/20Tue
1 stopDelta
7h 08mACK-ORD
$218
8/13Tue
1 stopDelta
5h 37mORD-ACK
8/20Tue
2 stopsDelta
10h 31mACK-ORD
$223
7/10Wed
1 stopJetBlue
6h 29mORD-MVY
7/17Wed
1 stopJetBlue
5h 09mMVY-ORD
$223
7/16Tue
1 stopJetBlue
5h 39mORD-ACK
7/24Wed
1 stopJetBlue
7h 38mACK-ORD
$224
8/13Tue
2 stopsDelta
7h 02mORD-ACK
8/20Tue
2 stopsDelta
10h 31mACK-ORD
$228
7/9Tue
1 stopAmerican Airlines
6h 00mORD-HYA
7/13Sat
1 stopAmerican Airlines
8h 28mHYA-ORD
$229
6/18Tue
1 stopUnited Airlines
7h 18mORD-ACK
6/21Fri
2 stopsUnited Airlines
16h 35mACK-ORD
$386
7/14Sun
nonstopUnited Airlines
2h 53mORD-ACK
7/24Wed
1 stopUnited Airlines
7h 58mACK-ORD
$489

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Recent one-way flight deals

8/10Sat
1 stopJetBlue
5h 49mORD-ACK
$94
8/23Fri
1 stopJetBlue
6h 49mORD-MVY
$130
6/25Tue
1 stopAmerican Airlines
5h 59mORD-HYA
$139
6/25Tue
2 stopsDelta
7h 04mORD-ACK
$166
6/22Sat
1 stopAmerican Airlines
21h 09mORD-ACK
$212
7/8Mon
1 stopDelta
4h 36mORD-MVY
$302
8/11Sun
2 stopsUnited Airlines
17h 23mORD-ACK
$317
6/20Thu
2 stops
8h 50mORD-HYA
$357
6/22Sat
3 stops
22h 34mORD-ACK
$394
7/15Mon
2 stopsUnited Airlines
17h 23mORD-ACK
$432

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Last minute flights from Chicago to Cape Cod and the Islands

Last minute flight, train and bus deals

6/7Fri
multi-stopDelta
5h 48mORD-MVY
6/11Tue
multi-stopDelta
6h 58mMVY-ORD
$627
6/7Fri
multi-stopDelta
5h 48mORD-MVY
6/11Tue
multi-stopDelta
7h 08mMVY-ORD
$632
6/9Sun
multi-stopJetBlue
6h 01mORD-MVY
6/14Fri
multi-stopJetBlue
4h 59mMVY-ORD
$681
6/9Sun
multi-stopDelta
5h 53mORD-MVY
6/14Fri
multi-stopDelta
6h 58mMVY-ORD
$716
6/7Fri
multi-stopUnited Airlines
14h 25mORD-ACK
6/9Sun
nonstopUnited Airlines
3h 17mACK-ORD
$803
6/7Fri
multi-stop
35h 18mORD-MVY
6/11Tue
multi-stop
29h 17mMVY-ORD
$816
6/9Sun
multi-stopJetBlue
4h 39mORD-HYA
6/10Mon
multi-stopJetBlue
8h 20mHYA-ORD
$825
6/7Fri
multi-stopUnited Airlines
5h 43mORD-ACK
6/9Sun
nonstopUnited Airlines
3h 17mACK-ORD
$828
6/7Fri
multi-stop
12h 10mORD-ACK
6/9Sun
multi-stop
30h 12mACK-ORD
$884
6/9Sun
multi-stopAmerican Airlines
5h 18mORD-HYA
6/10Mon
multi-stopAmerican Airlines
5h 49mHYA-ORD
$1,035

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Flights to Cape Cod and the Islands

Return flight deals:

Cape Cod and the Islands - Chicago

Cabin classes:

$172
$194
$283
$37