HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$53+ Cheap flights from Chicago (CHI) to Chesapeake, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Chesapeake with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chicago to Chesapeake are usually found in January or April, booked 73 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

Cheap flight deals from Chicago to Chesapeake

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Chesapeake (C6E). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$277
(American Airlines)

One-way from

$53
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$452
From Chicago (CHI) to Chesapeake
Search Deals
One-way flight from Chicago (CHI) to Chesapeake
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

Find flight deals from Chicago to Chesapeake

Cheapest flights from Chicago to Chesapeake
Explore the most affordable flight options available from Chicago to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 22, 2024.

This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:00 amORD - ORF
1 stop4h 13mDelta
Wed 1/112:55 pmORF - ORD
1 stop4h 45mDelta
Deal found 12/21$472
This United Airlines deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:15 amORD - ORF
Nonstop2h 23mUnited Airlines
Wed 1/111:20 amORF - ORD
Nonstop2h 40mUnited Airlines
Deal found 12/21$488
This American Airlines deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2711:33 amORD - ORF
1 stop6h 00mAmerican Airlines
Wed 1/19:52 amORF - ORD
1 stop7h 24mAmerican Airlines
Deal found 12/20$507
This Mytrip deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/238:30 amORD - ORF
1 stop13h 24mMultiple Airlines
Fri 1/104:31 pmORF - ORD
1 stop8h 01mMultiple Airlines
Deal found 12/20$517
This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3011:25 amORD - ORF
1 stop6h 35mSouthwest
Wed 1/11:00 pmORF - ORD
2 stops10h 00mSouthwest
Deal found 12/21$534
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/253:32 pmMDW - ORF
1 stop6h 17mDelta
Tue 12/314:41 pmORF - MDW
1 stop6h 25mDelta
Deal found 12/21$556
This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/228:25 pmMDW - ORF
Nonstop1h 55mSouthwest
Wed 1/17:30 amORF - MDW
Nonstop2h 10mSouthwest
Deal found 12/21$560
This FlightHub deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:00 amORD - ORF
1 stop17h 15mSpirit Airlines
Thu 1/29:45 amORF - ORD
1 stop13h 08mSpirit Airlines
Deal found 12/21$994

Find flights from Chicago to Chesapeake within your budget

Customize your flight search to find flights from Chicago to Chesapeake that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/11

6:54 pm-10:06 pm

Nonstop2h 12m

Norfolk

Sat 1/18

6:30 am-8:01 am

Nonstop2h 31m

$277

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 1/20

7:05 pm-10:05 pm

Nonstop2h 00m

Norfolk

Mon 1/27

7:15 am-8:35 am

Nonstop2h 20m

$278

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 1/26

10:29 am-9:36 pm

1 stop10h 07m

Norfolk

Tue 1/28

5:25 am-4:10 pm

1 stop11h 45m

$281

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 1/31

7:10 am-2:35 pm

1 stop6h 25m

Norfolk

Tue 2/4

6:35 am-8:05 am

Nonstop2h 30m

$282

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 1/26

6:00 am-12:13 pm

1 stop5h 13m

Norfolk

Tue 1/28

7:30 am-12:46 pm

1 stop6h 16m

$291

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 1/26

6:06 pm-3:36 pm

2 stops20h 30m

Norfolk

Tue 1/28

5:25 am-10:55 pm

2 stops18h 30m

$291

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 1/16

7:00 am-4:35 pm

2 stops8h 35m

Norfolk

Mon 1/20

4:20 pm-10:20 pm

1 stop7h 00m

$301

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 4/1

5:30 pm-12:03 am

1 stop5h 33m

Norfolk

Sat 4/5

6:55 am-1:20 pm

1 stop7h 25m

$394

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 2/25

8:30 am-5:34 pm

1 stop8h 04m

$53

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 2/24

7:08 pm-5:34 pm

1 stop21h 26m

$60

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 19 results
1
2

Best time to book a flight from Chicago to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Chesapeake

Get recent, data-driven insights about flights from Chicago to Chesapeake including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Chesapeake. Price data was last updated on December 20, 2024.

The best time to book flights from Chicago to Chesapeake is 73 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $281). Flying from Chicago to Chesapeake in June is currently the most expensive (average of $372). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to C6E?

Find hourly flight availability from Chicago to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 22, 2024.

When flying from Chicago to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Chesapeake. Price data was last updated on June 30, 2024.

Travelers seeking maximum savings on their Chicago to Chesapeake flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Chesapeake

Explore weekly flight availability from Chicago to Chesapeake. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 22, 2024.

The most flights from CHI to C6E are scheduled on a Monday (22 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chesapeake. Reviews last updated December 22, 2024.
To help decide which airline to fly from Chicago to Chesapeake, see what other customers have to say about Delta, American Airlines and Southwest. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Spirit Airlines
6.3
Okay
8,111 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Chesapeake one-way?

    One-way options have recently been found by users for as low as $53 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $91 and Southwest from $119 one-way.

  • What are the most reliable airlines from Chicago to Chesapeake?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Chesapeake on time: Air Wisconsin (94%), ANA (87%), Envoy Air (86%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $148. On average you can expect to pay $373. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $160.

  • Can I find deals for flights from Chicago to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Chicago to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Chesapeake.

  • Can I find deals for business class flights from Chicago to Chesapeake?

    Yes. Cheapflights offers flight deals from Chicago to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $281). Flying from Chicago to Chesapeake in June is currently the most expensive (average of $372). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Raleigh flights
Midway to Reagan-National flights
Midway to Dulles Intl flights
St. Louis to Dulles Intl flights
O'Hare Intl to Norfolk flights
O'Hare Intl to Richmond flights
St. Louis to Reagan-National flights
O'Hare Intl to Greensboro flights
Midway to Raleigh flights
St. Louis to Raleigh flights
O'Hare Intl to Roanoke flights
Midway to Norfolk flights
Midway to Richmond flights
Moline to Reagan-National flights
O'Hare Intl to Charlottesville flights
St. Louis to Norfolk flights
Moline to Dulles Intl flights
Midway to Greensboro flights
St. Louis to Richmond flights
Moline to Raleigh flights
Midway to Roanoke flights
Peoria to Dulles Intl flights
St. Louis to Greensboro flights
Peoria to Reagan-National flights
St. Louis to Charlottesville flights
Bloomington to Reagan-National flights
St. Louis to Roanoke flights
O'Hare Intl to Newport News flights
Midway to Charlottesville flights
Moline to Norfolk flights
Bloomington to Raleigh flights
Champaign to Reagan-National flights
Evansville to Reagan-National flights
Moline to Richmond flights
Bloomington to Dulles Intl flights
Peoria to Raleigh flights
O'Hare Intl to Lynchburg flights
St. Louis to Newport News flights
Evansville to Dulles Intl flights
Springfield to Reagan-National flights
Peoria to Roanoke flights
Peoria to Norfolk flights
O'Hare Intl to Blountville flights
St. Louis to Blountville flights
Champaign to Dulles Intl flights
Moline to Greensboro flights
Champaign to Raleigh flights
Midway to Blountville flights

Top 5 airlines flying from Chicago to Chesapeake

Discover the top 5 airlines that operate flights from Chicago to Chesapeake. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$201FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$117Average$385FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$193Average$406FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$200Average$367FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.