$71 Find Cheap Flights from Chicago to Chesapeake

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 Chesapeake departing on 5/27. 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

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Everything you should know

Cheapest round-trip
$298
Typical prices: $429-$321
JetBlue, Frontier
Mon 5/11Sat 5/16
ORD - ORF • 1 stop
Cheapest non-stop
$306
Typical prices: $685-$378
Southwest
Tue 6/2Sat 6/6
MDW - ORF • Non-stop
Arrival airport
You can't fly directly to Chesapeake. It is served by Norfolk (ORF), located 10.1 miles from Chesapeake.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Chesapeake (CHI-ORF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Chesapeake 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 Chesapeake

Mon, May 11 - Sat, May 16
Multiple Airlines Logo
9:49 am - 10:58 am
ORD
-
ORF
24h 09m
1 stop
Multiple Airlines Logo
11:42 am - 7:51 pm
ORF
-
ORD
9h 09m
1 stop
$298Multiple Airlines
Wed, May 6 - Sat, May 9
Frontier Logo
3:55 pm - 8:17 pm
ORD
-
ORF
27h 22m
1 stop
Frontier Logo
11:42 am - 7:51 pm
ORF
-
ORD
9h 09m
1 stop
$301Frontier
Wed, Jun 10 - Fri, Jun 12
Frontier Logo
1:50 pm - 11:26 am
ORD
-
ORF
20h 36m
1 stop
Frontier Logo
12:21 pm - 7:53 pm
ORF
-
ORD
8h 32m
1 stop
$302Frontier
Thu, Jul 23 - Tue, Jul 28
Multiple Airlines Logo
7:07 pm - 9:13 am
ORD
-
ORF
13h 06m
1 stop
Multiple Airlines Logo
6:12 pm - 12:25 pm
ORF
-
ORD
19h 13m
2 stops
$304Multiple Airlines
Sat, Jul 25 - Sat, Aug 1
Southwest Logo
6:25 pm - 9:25 pm
MDW
-
ORF
2h 00mnonstop
Southwest Logo
6:55 pm - 11:20 pm
ORF
-
MDW
5h 25m
1 stop
$305Southwest
Fri, Jun 12 - Mon, Jun 15
Frontier Logo
1:50 pm - 11:21 am
ORD
-
ORF
20h 31m
1 stop
Frontier Logo
9:35 pm - 7:53 pm
ORF
-
ORD
23h 18m
2 stops
$305Frontier
Wed, May 27 - Sat, May 30
American Airlines Logo
6:40 pm - 10:07 pm
ORD
-
ORF
2h 27mnonstop
American Airlines Logo
1:17 pm - 2:48 pm
ORF
-
ORD
2h 31mnonstop
$306American Airlines
Fri, May 15 - Sun, May 17
Multiple Airlines Logo
4:52 pm - 10:55 am
MDW
-
ORF
17h 03m
2 stops
Multiple Airlines Logo
8:49 pm - 3:57 pm
ORF
-
MDW
20h 08m
1 stop
$306Multiple Airlines
Thu, Jun 25 - Sun, Jun 28
Multiple Airlines Logo
2:46 pm - 9:13 am
MDW
-
ORF
17h 27m
2 stops
Multiple Airlines Logo
12:21 pm - 11:09 am
ORF
-
MDW
23h 48m
1 stop
$307Multiple Airlines
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
5:00 pm - 9:55 pm
MDW
-
ORF
3h 55m
1 stop
Southwest Logo
8:15 am - 9:25 am
ORF
-
MDW
2h 10mnonstop
$316Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway Airport to Norfolk

When to book flights from Chicago to Chesapeake

Are your dates flexible? Find out the best times to travel from Chicago to Chesapeake based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Chesapeake

  • Which airports will I be using when flying from Chicago to Chesapeake?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Chesapeake does not have its own airport so you’ll be flying into nearby Norfolk airport, which is 10.1 mi away.

  • How long does a flight from Chicago to Chesapeake take?

    Direct flights cover the 699 miles separating Chicago and Chesapeake in about 2h 00m.

  • How many flights are there between Chicago and Chesapeake?

    37 direct flights run between Chicago and Chesapeake on a daily basis. On average, there are about 260 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Chesapeake?

    Consider leaving on a Wednesday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Chesapeake?

    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 Chesapeake.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Chesapeake?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chesapeake 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 Chesapeake?

    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 Chesapeake 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 Chesapeake?

    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 Chesapeake from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Chesapeake?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Chesapeake found on KAYAK was with Frontier for $93. United Airlines offered a round-trip connection from $217 and Southwest from $230.

Top tips for finding cheap flights from Chicago to Chesapeake

  • There is no airport in Chesapeake. Instead, you’ll be flying into Norfolk Airport when flying between Chicago and Chesapeake.
  • The cheapest flight from Chicago to Chesapeake was found 72 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is December.

Reviews of the top 4 airlines serving Chicago to Chesapeake

 
Need help choosing which airline to fly with from Chicago to Chesapeake? 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
SouthwestOverall score based on 4315 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

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

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Everything you need to know for your flight from Chicago to Chesapeake

Complete your trip to Chesapeake with a hotel stay or car rental