$95 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.
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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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Flights Deals

Best Cape Cod and the Islands Flight Deals from Chicago

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

Nantucket
Nantucket1 stop$190
Boston
Boston1 stop$109
Nantucket
Nantucket1 stop$190
Boston
Boston1 stop$109

Cheap Flights from Chicago to Cape Cod and the Islands

 
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.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Cape Cod and the Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
JetBlue Logo
6:15 am - 3:23 pmORD-ACK
8h 08m1 stop
JetBlue Logo
4:34 pm - 11:25 pmACK-ORD
7h 51m1 stop
$190JetBlue
Find Deal
Sat, Jul 5 - Wed, Jul 9
JetBlue Logo
6:00 am - 11:53 amORD-ACK
4h 53m1 stop
JetBlue Logo
4:34 pm - 11:25 pmACK-ORD
7h 51m1 stop
$196JetBlue
Find Deal
Fri, Aug 1 - Sat, Aug 9
Delta Logo
6:00 am - 11:32 amORD-MVY
4h 32m1 stop
Delta Logo
3:08 pm - 9:31 pmMVY-ORD
7h 23m1 stop
$206Delta
Find Deal
Tue, Jun 3 - Sat, Jun 7
Delta Logo
6:00 am - 11:25 amORD-ACK
4h 25m1 stop
Delta Logo
4:45 pm - 10:21 pmACK-ORD
6h 36m1 stop
$206Delta
Find Deal
Wed, Jun 25 - Tue, Jul 1
American Airlines Logo
7:00 am - 5:38 pmORD-ACK
9h 38m1 stop
American Airlines Logo
2:09 pm - 7:26 pmACK-ORD
6h 17m1 stop
$317American Airlines
Find Deal
Fri, Aug 1 - Sat, Aug 9
American Airlines Logo
6:00 am - 12:38 pmORD-ACK
5h 38m1 stop
American Airlines Logo
5:45 pm - 7:49 pmACK-ORD
3h 04mnonstop
$359American Airlines
Find Deal
Tue, Jul 1 - Sat, Jul 5
United Airlines Logo
10:35 am - 2:29 pmORD-ACK
2h 54mnonstop
United Airlines Logo
4:32 pm - 6:55 pmACK-ORD
3h 23mnonstop
$543United Airlines
Find Deal
Sun, Jul 20 - Sun, Jul 27
 Logo
7:31 pm - 10:10 amORD-HYA
13h 39m1 stop
 Logo
3:50 pm - 8:00 amHYA-ORD
17h 10m1 stop
Wed, May 14 - Sun, May 18
 Logo
7:31 pm - 10:10 amORD-HYA
13h 39m1 stop
 Logo
11:00 am - 8:00 amHYA-ORD
22h 00m1 stop
Wed, May 28 - Wed, Jun 4
United Airlines Logo
7:15 am - 3:10 pmORD-ACK
6h 55m1 stop
United Airlines Logo
4:32 pm - 6:55 pmACK-ORD
3h 23mnonstop
$638United Airlines
Find Deal
Thu, Aug 14 - Sun, Aug 17
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Cape Cod and the Islands.

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 $353 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 $507.

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 $449, prices are generally cheapest when you fly direct.


Good to know

Low seasonFebruary
High seasonOctober
Cheapest flight$95
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 8% 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 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.

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

    The cheapest time of day to fly to Cape Cod and the Islands is generally in the afternoon, when round-trip flights cost $549 on average. The most expensive time of day to fly to Cape Cod and the Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $560.

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.
7.4
United AirlinesOverall score based on 8696 reviews
7.1Entertainment
8.1Crew
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

A bit rush for transit. Food and entertainment are not available

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Love the mosaic program, being able to move to an extra space seat for free is awesome

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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

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