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Find cheap flights from Chicago to Cape Cod and the Islands from $134

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 7/24. 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
Mon 6/3
Mon 6/10

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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

Boston
Boston1 stop$98

Good to know

Low season

January

High season

October

Cheapest flight

$134
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 2% increase in price.
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 10848 reviews
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

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

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

I was traveling with my 85 years old grandma and 60 years old mother. Which I requested to get a wheelchair. I went to the Delta Kiosk and asked for a wheelchair.  They brought a wheelchair and 2 minutes (without exaggerating, time is important for me as I am well disciplined with a military background) later they said that the wheelchair belongs to American Airlines, so we need to switch it.  We were like where is the other one so my grandma can use it? They are like, "it's on its way, she has to wait for the other one" I asked them why does she have to wait? Is it ok for her to sit on this one when the other one arrives. Answer was "NO". I guess lack of common sense was the issue. I started to explain to the agent that she can not stand still or wait. Finally, someone said that in spanish "she can not stand, let's wait for the other one" . Delta's wheelchair came, without an attendant or helper. They brought that wheelchair and left it in the middle of the airport. Nobody seemed to care. I had to push her to the gate. Then they finally realized that "wait a minute, there is something wrong with that". So they send someone, who later started harassing us, to tell us how he works for cash tips. Then a "Private Security Interviewer" approached us. I think his name was Carlos (His descriptions - tall for an average worker, ginger curly hair, wears glasses, overweight). He did not represent himself. All he did was show his badge for two seconds and when (later on) I asked him what his name was, he said "I already told you at the beginning". At that point we were waiting to be called at the Delta Kiosk (this is prior to the Customs first check in point). So, Delta Airlines hired "Private security interviewers" to make sure that nobody brings anything illegally to the US. Which is great, makes me feel safe and secure. But, it does not serve the purpose. Let me explain to you why. These interviewers do not know what they are doing or saying and you can clearly see that. They think that they are CBP or Immigration officers. They will get angry If you ask them any questions. Then they will put all these stickers on the back of your passport like they caught "Pablo Escobar". At one point I was sarcastic and told the interviewer that "I like those stickers, It's my hobby and I am collecting them. Can I have more of those?"  and interviewers eyes and brain goes like "error 404". He did not know how to react or respond to that. Then he flags my itinerary on his iPad. Trying to give me a hard time since I asked him about his name, so I can call him by his name. But of course that did not change the fact that his lack of english made everything even harder. After 45 mins of wait and clearing the "Private Security Interviewer" you would think that we are going to be all set to depart. I was wrong. We waited in line to go through the security line, just like other citizens. No wheelchair, disability, seniority etc were important for her. They treat us like she is in her twenties.  On several occasions they forced her to stand up. She was like "I swear to God that I can not walk, my son I wish I could walk, but I can not". They did not seem like they cared. Then finally they realized that she is legit disabled. They let her pass on a wheelchair. At the gate, Carlos showed up to make sure that I am going through the secondary check. They pulled me to the secondary check. And started asking me about my luggage. My response was "I only have one carry-on bag, to make everyone's (including my life) life easier". They asked the same question over again "Sir, do you just have only one bag?" I replied saying "Yes". She did not believe me and said "Just only one". So, I thought she did not believe me and I said "Yes, Si, Si, solo uno". She looked at me and then turned to the agent (Carlos) and stared at him like "did you not ask him about his bags, did you not know that he only had one carry on?". I am sorry to say that but they just looked like a bunch of idiots who do not know what they are doing. Finally they released me after a minute of secondary check. Meanwhile everyone is boarding and my grandma is waiting on her wheelchair. Then we approached the gate agent and I asked her if I could sit next to my family, if they had any seats available. She replied that "I can not change any seat at the gate, I do not have any authority". I replied "I understood". We got on the plane last and I asked our flight attendant if I could change my seat to be next to my family. FYI, their seats were 10 B and C, mine was the 35 D. Meanwhile there were empty seats on 10 D and F. Even flight attendants surprisingly said that "why did she put you all the way back, while we had 1/2 full flight. I will go and ask her". Our flight attendant was great and he made sure that I am next to my family. He went above and beyond and he gave the closest seat to the. Flight was good. Delta Airlines failed to bring the wheelchair when we arrived. Excuse was "Gate changed, that is why". I walked outside and grabbed an empty wheelchair. I put my grandma and brought her to the Customs. Then a Delta Airline worker approaches me and says that you can not move this wheelchair, it belongs to the gate. We will bring you a new one. A CBP officer heard our conversation and jumped in and said, "wait a minute you want her (pointed my grandma) to wait here while you bring her wheelchair?". He (delta worker) responded "yes sir". But when he talks to me, no sir, nothing. The CBP officer goes "Nope, she is not waiting here and I will make sure to pull her wheelchair". If that officer was not there we probably would have had to wait and be forced to change the wheelchair. The CBP officer, again the CBP officer, not the Delta employee, pushed our wheelchairs to the gate. Sincerely,

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.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

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.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

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

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Cape Cod and the Islands

Recent round-trip flight deals

6/24Mon
1 stopDelta
7h 14mORD-ACK
7/2Tue
1 stopDelta
7h 50mACK-ORD
$218
7/11Thu
1 stopAmerican Airlines
6h 26mORD-ACK
7/18Thu
1 stopAmerican Airlines
5h 31mACK-ORD
$248
8/16Fri
1 stopAmerican Airlines
4h 27mORD-ACK
8/20Tue
2 stopsAmerican Airlines
7h 55mACK-ORD
$253
8/24Sat
1 stopDelta
23h 59mORD-ACK
8/27Tue
1 stopDelta
6h 37mACK-ORD
$255
8/24Sat
1 stopDelta
20h 10mORD-ACK
8/27Tue
2 stopsDelta
7h 31mACK-ORD
$260
6/24Mon
1 stopDelta
7h 14mORD-ACK
7/3Wed
1 stopDelta
7h 30mACK-ORD
$263
6/28Fri
1 stopJetBlue
6h 24mORD-MVY
7/1Mon
1 stopJetBlue
5h 14mMVY-ORD
$381
7/1Mon
1 stopJetBlue
5h 34mORD-ACK
7/5Fri
1 stopJetBlue
7h 38mACK-ORD
$442
6/26Wed
1 stopUnited Airlines
7h 18mORD-ACK
6/30Sun
nonstopUnited Airlines
3h 17mACK-ORD
$527
7/17Wed
1 stopUnited Airlines
7h 23mORD-ACK
7/21Sun
nonstopUnited Airlines
3h 17mACK-ORD
$590

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Recent one-way flight deals

7/24Wed
1 stopJetBlue
7h 16mORD-ACK
$134
8/10Sat
2 stopsDelta
17h 26mMDW-ACK
$147
7/6Sat
1 stopAmerican Airlines
4h 42mORD-HYA
$154
8/6Tue
2 stopsDelta
24h 22mMDW-ACK
$168
5/28Tue
1 stopDelta
4h 43mORD-MVY
$193
7/6Sat
1 stopJetBlue
7h 28mORD-MVY
$211
7/25Thu
1 stopJetBlue
3h 54mORD-ACK
$217
6/15Sat
1 stopAmerican Airlines
19h 49mORD-HYA
$226
5/26Sun
2 stopsUnited Airlines
24h 55mORD-ACK
$239
5/25Sat
2 stopsUnited Airlines
14h 41mORD-ACK
$268

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Last minute flights from Chicago to Cape Cod and the Islands

Last minute flight, train and bus deals

5/9Thu
multi-stop
11h 04mORD-PVC
5/11Sat
multi-stop
11h 23mPVC-ORD
$596
5/9Thu
multi-stop
11h 04mORD-PVC
5/11Sat
multi-stop
6h 54mPVC-ORD
$605
5/9Thu
multi-stop
16h 31mORD-PVC
5/11Sat
multi-stop
14h 38mPVC-ORD
$669

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Flights to Cape Cod and the Islands

Return flight deals:

Cape Cod and the Islands - Chicago

Cabin classes:

$234
$328
$256
$27