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Find cheap flights from Chicago to Chesapeake from $58

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 8/8. 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
Fri 7/12
Fri 7/19

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Good to know

Low season

January

High season

July

Cheapest flight

$58
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 12% 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 15m.

  • How many flights are there between Chicago and Chesapeake?

    15 direct flights run between Chicago and Chesapeake on a daily basis. On average, there are about 108 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 United Airlines for $58. United Airlines offered a round-trip connection from $115 and Spirit Airlines from $121.

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 10277 reviews
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
8.0Entertainment
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

Book cheap flights from Chicago to Chesapeake

Recent round-trip flight deals

8/17Sat
nonstopUnited Airlines
2h 15mORD-ORF
8/24Sat
nonstopUnited Airlines
2h 20mORF-ORD
$115
9/16Mon
1 stopSpirit Airlines
13h 15mORD-ORF
9/21Sat
1 stopSpirit Airlines
10h 12mORF-ORD
$121
7/15Mon
1 stopSpirit Airlines
18h 28mORD-ORF
8/6Tue
1 stopSpirit Airlines
13h 15mORF-ORD
$140
7/17Wed
1 stopFrontier
28h 25mMDW-ORF
8/8Thu
1 stopFrontier
21h 13mORF-MDW
$161
8/17Sat
1 stopUnited Airlines
6h 36mORD-ORF
8/24Sat
nonstopUnited Airlines
2h 20mORF-ORD
$164
9/12Thu
1 stopFrontier
10h 17mMDW-ORF
9/15Sun
1 stopFrontier
26h 43mORF-MDW
$169
8/17Sat
1 stopDelta
7h 07mMDW-ORF
8/24Sat
1 stopDelta
3h 34mORF-MDW
$176
8/8Thu
1 stopDelta
6h 55mORD-ORF
8/11Sun
1 stopDelta
3h 51mORF-ORD
$176
7/4Thu
1 stopAmerican Airlines
5h 27mORD-ORF
7/9Tue
nonstopAmerican Airlines
2h 23mORF-ORD
$287
7/10Wed
nonstopAmerican Airlines
2h 25mORD-ORF
7/17Wed
nonstopAmerican Airlines
2h 23mORF-ORD
$315

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Recent one-way flight deals

8/8Thu
nonstopUnited Airlines
2h 18mORD-ORF
$58
9/3Tue
1 stopFrontier
8h 17mORD-ORF
$65
7/16Tue
1 stopSpirit Airlines
8h 58mORD-ORF
$74
8/26Mon
1 stopSpirit Airlines
22h 24mORD-ORF
$77
9/3Tue
1 stopDelta
5h 41mMDW-ORF
$88
6/20Thu
1 stop
15h 41mORD-ORF
$93
6/29Sat
3 stops
24h 16mORD-ORF
$147
9/3Tue
nonstopAmerican Airlines
2h 29mORD-ORF
$148
7/12Fri
nonstopAmerican Airlines
2h 25mORD-ORF
$178
11/12Tue
1 stopDelta
7h 06mMDW-ORF
$187

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Last minute flights from Chicago to Chesapeake

Last minute flight, train and bus deals

6/14Fri
multi-stopFrontier
5h 38mORD-ORF
6/18Tue
multi-stopFrontier
26h 31mORF-ORD
$285
6/12Wed
multi-stopFrontier
5h 38mORD-ORF
6/20Thu
multi-stopFrontier
13h 07mORF-ORD
$288
6/16Sun
multi-stopSpirit Airlines
18h 09mORD-ORF
6/20Thu
multi-stopSpirit Airlines
18h 47mORF-ORD
$350
6/16Sun
multi-stopSpirit Airlines
7h 50mORD-ORF
6/21Fri
multi-stopSpirit Airlines
18h 47mORF-ORD
$393
6/16Sun
nonstopAmerican Airlines
2h 18mORD-ORF
6/20Thu
nonstopAmerican Airlines
2h 23mORF-ORD
$561
6/16Sun
nonstopAmerican Airlines
2h 18mORD-ORF
6/20Thu
multi-stopAmerican Airlines
4h 50mORF-ORD
$571
6/13Thu
nonstopUnited Airlines
2h 15mORD-ORF
6/19Wed
nonstopUnited Airlines
2h 22mORF-ORD
$635
6/13Thu
nonstopUnited Airlines
2h 18mORD-ORF
6/17Mon
multi-stopUnited Airlines
4h 35mORF-ORD
$645
6/12Wed
multi-stopDelta
5h 34mMDW-ORF
6/18Tue
multi-stopDelta
5h 55mORF-MDW
$674
6/12Wed
multi-stopDelta
5h 34mMDW-ORF
6/15Sat
multi-stopDelta
3h 48mORF-MDW
$748

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Flights to Chesapeake

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