$134 Find Cheap Flights from Chicago to Cape Cod and the Islands

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 6/24. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Cape Cod and the Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cape Cod and the Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Cape Cod and the Islands, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Cape Cod and the Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Cape Cod and the Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Cape Cod and the Islands

Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
5:00 am - 12:15 pm
ORD
-
HYA
6h 15m
1 stop
American Airlines Logo
6:08 pm - 11:30 pm
HYA
-
ORD
6h 22m
1 stop
$265American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
8:00 am - 11:55 am
ORD
-
ACK
2h 55mnonstop
American Airlines Logo
5:11 pm - 11:30 pm
ACK
-
ORD
7h 19m
1 stop
$272American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
6:00 am - 2:24 pm
ORD
-
HYA
7h 24m
1 stop
American Airlines Logo
6:08 pm - 11:30 pm
HYA
-
ORD
6h 22m
1 stop
$282American Airlines
Sat, Jun 20 - Sat, Jun 27
American Airlines Logo
6:00 am - 2:42 pm
ORD
-
ACK
7h 42m
1 stop
American Airlines Logo
5:09 pm - 11:30 pm
ACK
-
ORD
7h 21m
1 stop
$282American Airlines
Tue, Jun 30 - Fri, Jul 3
Delta Logo
7:05 am - 3:48 pm
ORD
-
ACK
7h 43m
1 stop
Delta Logo
12:06 pm - 4:45 pm
ACK
-
ORD
5h 39m
1 stop
$290Delta
Tue, Jun 30 - Fri, Jul 3
Delta Logo
7:05 am - 3:48 pm
ORD
-
ACK
7h 43m
1 stop
Delta Logo
12:06 pm - 8:31 pm
ACK
-
ORD
9h 25m
2 stops
$296Delta
Tue, Sep 1 - Wed, Sep 2
JetBlue Logo
9:39 am - 4:09 pm
ORD
-
MVY
5h 30m
1 stop
JetBlue Logo
5:05 pm - 9:55 pm
MVY
-
ORD
5h 50m
1 stop
$401JetBlue
Wed, May 27 - Fri, May 29
JetBlue Logo
8:50 am - 3:59 pm
ORD
-
PVC
6h 09m
1 stop
JetBlue Logo
11:57 am - 7:35 pm
PVC
-
ORD
8h 38m
1 stop
$665JetBlue
Fri, Jul 10 - Mon, Jul 13
Multiple Airlines Logo
10:56 am - 6:30 pm
ORD
-
PVC
6h 34m
1 stop
Multiple Airlines Logo
2:20 pm - 7:25 pm
PVC
-
ORD
6h 05m
1 stop
$729Multiple Airlines
Sat, May 23 - Wed, May 27
Multiple Airlines Logo
10:45 am - 6:55 pm
ORD
-
PVC
7h 10m
2 stops
Multiple Airlines Logo
2:13 pm - 7:35 pm
PVC
-
ORD
6h 22m
1 stop
$735Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Cape Cod and the Islands flights

Get data-powered insights and trends into flights from Chicago to Cape Cod and the Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Cape Cod and the Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Cape Cod and the Islands from Chicago O'Hare Intl Airport found in the last 72 hours was to Hyannis, at $394 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Nantucket (ACK), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $597.

What is the cheapest time of day to fly to Cape Cod and the Islands?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Cape Cod and the Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Cape Cod and the Islands is generally at night, when round-trip flights cost $214 on average. Morning departures are around 15% cheaper than evening flights, on average. The most expensive time of day to fly to Cape Cod and the Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $296.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Cape Cod and the Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $479, prices are generally cheapest when you fly direct.

What’s the cheapest day of the week to fly from Chicago to Cape Cod and the Islands?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Cape Cod and the Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Cape Cod and the Islands on a Wednesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Friday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Cape Cod and the Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Cape Cod and the Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Cape Cod and the Islands, you should book around 2 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$134
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago to Hyannis

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

Reviews of the top 3 airlines serving from Chicago to Cape Cod and the Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Cape Cod and the Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.9
DeltaOverall score based on 8445 reviews
7.8Comfort
7.8Entertainment
8.1Boarding
7.2Food
8.5Crew
Airline reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

6.0 Goodrghinftl, May 2026
FWA - ATL
Read more Delta reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight to Cape Cod and the Islands

Information on your arrival and departure airports