$136 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 10/7. 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

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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Cheap Flights from Chicago to Cape Cod and the Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$131
Boston
Bostonnonstop$131

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

Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
7:30 am - 7:15 pmORD-EWB
10h 45m1 stop
Multiple Airlines Logo
2:00 pm - 8:00 amEWB-ORD
19h 00m1 stop
$384Multiple Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
7:30 am - 7:15 pmORD-EWB
10h 45m1 stop
Multiple Airlines Logo
2:00 pm - 2:25 pmEWB-ORD
25h 25m2 stops
$394Multiple Airlines
Find Deal
Mon, Feb 16 - Fri, Feb 20
JetBlue Logo
12:10 pm - 6:39 pmORD-HYA
5h 29m1 stop
JetBlue Logo
12:07 pm - 5:31 pmHYA-ORD
6h 24m1 stop
$425JetBlue
Find Deal
Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
6:00 am - 7:15 pmORD-EWB
12h 15m2 stops
Multiple Airlines Logo
2:00 pm - 9:36 amEWB-ORD
20h 36m2 stops
$439Multiple Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 28
JetBlue Logo
10:08 am - 6:39 pmORD-HYA
7h 31m1 stop
JetBlue Logo
12:07 pm - 5:55 pmHYA-ORD
6h 48m1 stop
$445JetBlue
Find Deal
Fri, Oct 24 - Wed, Oct 29
JetBlue Logo
6:45 am - 6:39 pmORD-HYA
10h 54m2 stops
JetBlue Logo
7:58 am - 5:55 pmHYA-ORD
10h 57m1 stop
$500JetBlue
Find Deal
Fri, Oct 24 - Wed, Oct 29
JetBlue Logo
10:08 am - 6:39 pmORD-HYA
7h 31m1 stop
JetBlue Logo
7:58 am - 5:55 pmHYA-ORD
10h 57m1 stop
$545JetBlue
Find Deal
Sun, Oct 5 - Thu, Oct 9
JetBlue Logo
9:51 am - 6:45 pmORD-HYA
7h 54m1 stop
JetBlue Logo
10:16 am - 8:51 pmHYA-ORD
11h 35m1 stop
$597JetBlue
Find Deal
Sun, Oct 5 - Wed, Oct 8
JetBlue Logo
9:51 am - 3:46 pmORD-PVC
4h 55m1 stop
JetBlue Logo
10:31 am - 6:18 pmPVC-ORD
8h 47m1 stop
$615JetBlue
Find Deal
Mon, Oct 6 - Fri, Oct 10
JetBlue Logo
10:08 am - 5:38 pmORD-HYA
6h 30m1 stop
JetBlue Logo
10:16 am - 8:50 pmHYA-ORD
11h 34m1 stop
$617JetBlue
Find Deal
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 $276 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Hyannis (HYA), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $276.

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 $402, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Cape Cod and the Islands?

To calculate monthly average prices, KAYAK takes all prices for each month 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 median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Cape Cod and the Islands is September, when tickets cost $197 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $272 and $258 respectively.

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 Thursday 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 3 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$136
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 4% 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 at night, when round-trip flights cost $225 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 afternoon, which is peak travel time and where the average cost of a ticket is $299.

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.
7.4
United AirlinesOverall score based on 8922 reviews
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

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.

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.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

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

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