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Find cheap flights from Chicago to Chesapeake from $52

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 5/29. 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
0 bags
Sat 6/8
Sat 6/15

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Good to know

Low season

January

High season

July

Cheapest flight

$52
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare 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?

    20 direct flights run between Chicago and Chesapeake on a daily basis. On average, there are about 144 departures each week.

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

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

  • 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 Spirit Airlines for $52. Frontier offered a round-trip connection from $160 and Spirit Airlines from $227.

See more FAQs

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 79 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 May, June and July. The cheapest month to fly is September.
See more tips

Top 5 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
DeltaOverall score based on 10778 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Book cheap flights from Chicago to Chesapeake

Recent round-trip flight deals

9/21Sat
1 stopFrontier
20h 53mMDW-ORF
9/24Tue
1 stopFrontier
18h 35mORF-MDW
$160
7/24Wed
1 stopFrontier
8h 23mMDW-ORF
7/29Mon
1 stopFrontier
6h 55mORF-MDW
$169
5/24Fri
2 stopsSpirit Airlines
16h 22mORD-ORF
5/28Tue
2 stopsSpirit Airlines
21h 08mORF-ORD
$227
5/24Fri
1 stopSpirit Airlines
15h 21mORD-ORF
5/28Tue
1 stopSpirit Airlines
12h 40mORF-ORD
$228
6/5Wed
nonstopAmerican Airlines
2h 18mORD-ORF
6/12Wed
nonstopAmerican Airlines
2h 23mORF-ORD
$291
6/5Wed
1 stopAmerican Airlines
5h 06mORD-ORF
6/11Tue
nonstopAmerican Airlines
2h 23mORF-ORD
$299
6/3Mon
nonstopUnited Airlines
2h 15mORD-ORF
6/5Wed
nonstopUnited Airlines
2h 22mORF-ORD
$306
6/5Wed
1 stopDelta
6h 00mMDW-ORF
6/12Wed
1 stopDelta
7h 35mORF-MDW
$310
7/9Tue
1 stopDelta
4h 34mORD-ORF
7/17Wed
1 stopDelta
7h 16mORF-ORD
$310
6/3Mon
nonstopUnited Airlines
2h 15mORD-ORF
6/5Wed
1 stopUnited Airlines
6h 35mORF-ORD
$315

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Recent one-way flight deals

5/29Wed
1 stopSpirit Airlines
15h 04mORD-ORF
$52
6/12Wed
1 stopFrontier
5h 38mORD-ORF
$58
5/18Sat
1 stop
13h 07mORD-ORF
$73
6/6Thu
1 stop
15h 41mORD-ORF
$84
5/29Wed
nonstopAmerican Airlines
2h 26mORD-ORF
$146
5/29Wed
1 stopDelta
6h 01mMDW-ORF
$155
8/17Sat
1 stopDelta
4h 28mMDW-ORF
$157
6/16Sun
nonstopUnited Airlines
2h 15mORD-ORF
$178
6/16Sun
1 stopAmerican Airlines
4h 05mORD-ORF
$188
6/8Sat
nonstopUnited Airlines
2h 15mORD-ORF
$213

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Last minute flights from Chicago to Chesapeake

Last minute flight, train and bus deals

5/14Tue
multi-stopSpirit Airlines
24h 39mORD-ORF
5/22Wed
multi-stopSpirit Airlines
27h 25mORF-ORD
$153
5/14Tue
multi-stopSpirit Airlines
15h 05mORD-ORF
5/15Wed
multi-stopSpirit Airlines
13h 51mORF-ORD
$217
5/11Sat
multi-stopFrontier
23h 29mMDW-ORF
5/14Tue
multi-stopFrontier
14h 42mORF-MDW
$347
5/11Sat
multi-stopFrontier
26h 31mORD-ORF
5/14Tue
multi-stopFrontier
28h 00mORF-ORD
$347
5/14Tue
nonstopUnited Airlines
2h 16mORD-ORF
5/15Wed
nonstopUnited Airlines
2h 25mORF-ORD
$561
5/13Mon
nonstopAmerican Airlines
2h 26mORD-ORF
5/15Wed
nonstopAmerican Airlines
2h 29mORF-ORD
$563
5/14Tue
nonstopAmerican Airlines
2h 26mORD-ORF
5/15Wed
multi-stopAmerican Airlines
4h 38mORF-ORD
$569
5/14Tue
multi-stopDelta
6h 46mMDW-ORF
5/15Wed
multi-stopDelta
5h 07mORF-MDW
$580
5/13Mon
nonstopUnited Airlines
2h 16mORD-ORF
5/14Tue
nonstopUnited Airlines
2h 25mORF-ORD
$607
5/14Tue
multi-stopDelta
5h 43mMDW-ORF
5/15Wed
multi-stopDelta
5h 07mORF-MDW
$654

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Flights to Chesapeake

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