HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$71+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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.

Cheapflights Tip: The best prices from Chicago to Chesapeake are usually found in September or November, booked 73 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from Chicago to Chesapeake

Keep the following information in mind while searching for Chicago to Chesapeake flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$199
(Kiwi.com)

One-way from

$71
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$343
From Chicago (CHI) to Chesapeake
Search Deals
One-way flight from Chicago (CHI) to Chesapeake
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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 septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/148:05 amMDW - ORF
1 stop7h 44mFrontier
mar. 10/216:15 pmORF - MDW
1 stop20h 23mFrontier
Deal found 9/15$199
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/95:05 amORD - ORF
1 stop8h 49mMultiple Airlines
dom. 10/125:24 amORF - ORD
1 stop6h 26mMultiple Airlines
Deal found 9/15$200
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/156:58 pmORD - ORF
1 stop13h 04mMultiple Airlines
lun. 10/204:57 pmORF - ORD
1 stop25h 56mMultiple Airlines
Deal found 9/15$207
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/235:05 amORD - ORF
1 stop8h 49mMultiple Airlines
lun. 10/275:24 amORF - ORD
1 stop6h 26mMultiple Airlines
Deal found 9/15$208
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1011:55 amORD - ORF
1 stop9h 51mMultiple Airlines
sáb. 10/181:22 pmORF - ORD
1 stop11h 07mMultiple Airlines
Deal found 9/16$210
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/411:21 amMDW - ORF
1 stop28h 36mFrontier
lun. 10/612:19 pmORF - MDW
1 stop12h 22mFrontier
Deal found 9/15$212
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/1611:55 amORD - ORF
1 stop9h 51mSpirit Airlines
jue. 10/235:24 amORF - ORD
1 stop6h 26mSpirit Airlines
Deal found 9/16$213
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/285:10 amORD - ORF
1 stop5h 09mMultiple Airlines
vie. 10/35:20 amORF - ORD
1 stop6h 32mMultiple Airlines
Deal found 9/15$215
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:00 amORD - ORF
1 stop9h 39mMultiple Airlines
dom. 11/23:49 pmORF - ORD
1 stop10h 10mMultiple Airlines
Deal found 9/15$216
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/236:20 amMDW - ORF
1 stop7h 34mMultiple Airlines
lun. 10/275:24 amORF - MDW
2 stops11h 45mMultiple Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/156:58 pmORD - ORF
1 stop13h 04mMultiple Airlines
mar. 10/217:00 amORF - ORD
1 stop28h 08mMultiple Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/25:50 pmORD - ORF
1 stop16h 34mFrontier
dom. 10/55:47 pmORF - ORD
2 stops17h 44mFrontier
Deal found 9/14$219

Cheapflights Fare Finder

 
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 septiembre 16, 2025.
Use the filters below to find and compare flights from Chicago to Chesapeake that are best for you.

Fly from

Chicago

Fly to

Chesapeake

Route

Depart

Return

Price

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

mar. 10/14

8:05 am-4:49 pm

1 stop7h 44m

Norfolk

mar. 10/21

6:15 pm-1:38 pm

1 stop20h 23m

$199

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

sáb. 10/4

11:21 am-4:57 pm

1 stop28h 36m

Norfolk

lun. 10/6

12:19 pm-11:41 pm

1 stop12h 22m

$212

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

mar. 10/14

8:05 am-4:49 pm

1 stop7h 44m

Norfolk

lun. 10/20

4:57 pm-1:38 pm

2 stops21h 41m

$227

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

mié. 10/15

6:58 pm-9:02 am

1 stop13h 04m

Norfolk

dom. 10/19

12:39 pm-2:41 pm

1 stop27h 02m

$227

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 10/30

6:54 pm-4:39 pm

1 stop20h 45m

Norfolk

dom. 11/2

5:24 am-1:59 pm

2 stops9h 35m

$228

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 9/25

6:30 am-4:43 pm

1 stop9h 13m

Norfolk

lun. 9/29

5:20 am-5:39 pm

1 stop13h 19m

$237

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 11/13

5:25 am-1:15 pm

1 stop6h 50m

Norfolk

dom. 11/16

8:01 am-5:04 pm

1 stop10h 03m

$237

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

sáb. 10/18

6:58 pm-9:02 am

1 stop13h 04m

Norfolk

lun. 10/20

5:24 am-11:39 pm

2 stops19h 15m

$239

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

sáb. 12/6

6:05 am-7:37 pm

1 stop12h 32m

Norfolk

lun. 12/8

8:09 pm-9:23 am

1 stop14h 14m

$241

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

jue. 10/23

6:20 am-2:54 pm

1 stop7h 34m

Norfolk

lun. 10/27

7:00 am-4:09 pm

1 stop10h 09m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 42 results
1
2
3
...
5

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.

Cheapflights Insights

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

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 September 12, 2025.

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 March is currently the most expensive (average of $351). 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 septiembre 16, 2025.

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 September 14, 2025.

Travelers seeking maximum savings on their Chicago to Chesapeake flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday evenings 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 septiembre 16, 2025.

The most flights from CHI to C6E are scheduled on a Sunday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 on average).

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 septiembre 16, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Chesapeake to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Chesapeake?

    For as low as $199, Frontier can have you in Chesapeake from Chicago in 7h 44m. The distance from Chicago to Chesapeake is about 702 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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: Republic Airways (80%), GoJet (77%), United Airlines (75%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $135. On average you can expect to pay $337. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $172.

  • 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 March is currently the most expensive (average of $351). 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 Reagan-National flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl flights
Midway to Reagan-National flights
Midway to Raleigh flights
St. Louis to Dulles Intl flights
O'Hare Intl to Richmond flights
St. Louis to Reagan-National flights
O'Hare Intl to Norfolk flights
O'Hare Intl to Charlottesville flights
O'Hare Intl to Greensboro flights
O'Hare Intl to Roanoke flights
Midway to Richmond flights
St. Louis to Raleigh flights
Midway to Norfolk flights
Midway to Greensboro flights
St. Louis to Richmond flights
St. Louis to Charlottesville flights
Midway to Charlottesville flights
Moline to Dulles Intl flights
St. Louis to Norfolk flights
Peoria to Reagan-National flights
Peoria to Dulles Intl flights
Midway to Roanoke flights
St. Louis to Greensboro flights
Moline to Reagan-National flights
Peoria to Raleigh flights
Moline to Raleigh flights
Moline to Richmond flights
Bloomington to Raleigh flights
O'Hare Intl to Blountville flights
Peoria to Richmond flights
Evansville to Dulles Intl flights
Bloomington to Reagan-National flights
Bloomington to Dulles Intl flights
St. Louis to Roanoke flights
O'Hare Intl to Staunton flights
Evansville to Reagan-National flights
O'Hare Intl to Lynchburg flights
St. Louis to Blountville flights
O'Hare Intl to Salisbury flights
O'Hare Intl to Newport News flights
Peoria to Greensboro flights
Moline to Norfolk flights
Moline to Charlottesville flights
Midway to Blountville flights
Evansville to Raleigh flights
Peoria to Norfolk flights
Moline to Roanoke 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$213Average$369FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$395FlexibilityNo 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.