$79 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 8/25. 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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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

Mon, Aug 31 - Wed, Sep 2
JetBlue Logo
6:00 am - 3:24 pm
ORD
-
ACK
8h 24m
1 stop
JetBlue Logo
12:02 pm - 5:35 pm
ACK
-
ORD
6h 33m
1 stop
$166JetBlue
Tue, Aug 25 - Sat, Aug 29
JetBlue Logo
6:00 am - 3:13 pm
ORD
-
HYA
8h 13m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$167JetBlue
Sat, Aug 29 - Tue, Sep 1
JetBlue Logo
9:40 am - 4:12 pm
ORD
-
MVY
5h 32m
1 stop
JetBlue Logo
5:05 pm - 9:58 pm
MVY
-
ORD
5h 53m
1 stop
$174JetBlue
Thu, Aug 27 - Mon, Aug 31
JetBlue Logo
9:40 am - 3:24 pm
ORD
-
ACK
4h 44m
1 stop
JetBlue Logo
4:21 pm - 9:58 pm
ACK
-
ORD
6h 37m
1 stop
$182JetBlue
Wed, Aug 12 - Sat, Aug 15
JetBlue Logo
9:35 am - 3:13 pm
ORD
-
HYA
4h 38m
1 stop
JetBlue Logo
4:53 pm - 9:58 pm
HYA
-
ORD
6h 05m
1 stop
$183JetBlue
Thu, Jul 9 - Mon, Jul 13
American Airlines Logo
6:37 am - 12:15 pm
ORD
-
HYA
4h 38m
1 stop
American Airlines Logo
6:22 pm - 11:30 pm
HYA
-
ORD
6h 08m
1 stop
$275American Airlines
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
8:19 am - 3:26 pm
ORD
-
ACK
6h 07m
1 stop
American Airlines Logo
3:41 pm - 10:30 pm
ACK
-
ORD
7h 49m
1 stop
$282American Airlines
Mon, Aug 31 - Wed, Sep 2
Delta Logo
6:00 am - 11:13 am
ORD
-
MVY
4h 13m
1 stop
Delta Logo
11:53 am - 8:30 pm
MVY
-
ORD
9h 37m
2 stops
$322Delta
Wed, Jul 22 - Sat, Jul 25
Multiple Airlines Logo
6:05 am - 3:25 pm
ORD
-
PVC
8h 20m
1 stop
Multiple Airlines Logo
4:20 pm - 10:20 pm
PVC
-
ORD
7h 00m
1 stop
$722Multiple Airlines
Tue, Sep 1 - Sun, Sep 6
Multiple Airlines Logo
6:00 am - 4:40 pm
ORD
-
PVC
9h 40m
2 stops
Multiple Airlines Logo
6:45 am - 4:16 pm
PVC
-
ORD
10h 31m
2 stops
$758Multiple 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 5 days was to Hyannis, at $255 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to West Tisbury (MVY), and the cheapest round-trip airline ticket found on this route in the last 5 days was $369.

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 $230 on average. Morning departures are around 13% 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 $298.

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 $497, 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 Saturday 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 26% 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$79
Best time to beat the crowds with an average 16% drop in price.
Flight from Chicago to West Tisbury

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.

  • How many flights are there between Chicago O'Hare Intl Airport and Cape Cod and the Islands per day?

    Each day, there are between 1 and 4 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Cape Cod and the Islands, with an average flight time of 2h 52m. The most common departure time is 11:00 am and most flights take off in the morning, while the most flights land at Nantucket. Each week, there are 5 flights. The most frequent day of departure is Saturday, when 80% of all weekly flights depart. The fewest flights depart on a Sunday.

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.
7.8
DeltaOverall score based on 8454 reviews
8.1Boarding
8.5Crew
7.8Entertainment
7.8Comfort
7.2Food
Airline reviews

Very easy to use and convenient, you can perform any action within the same portal

10.0 ExcellentMurat, Apr 2026
ORD - LGA
Read more Delta reviews

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

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.

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

Delta airlines charge $ 30,oo US DOLLARS for the check in for a suitcase in the baggage hold

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

The plane was freezing cold. Normally I’m fine on planes but I needed to toss a sweatshirt on this time.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

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.

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

Information on your arrival and departure airports