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Chesapeake

$45+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Chesapeake are usually found in September or January, booked 70 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap 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 23, 2025.

This Expedia deal was found by Cheapflights users on 12/22. 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.
Fri 12/266:12 amMDW - ORF
1 stop6h 27mFrontier
Wed 12/3111:44 amORF - MDW
1 stop11h 28mFrontier
Deal found 12/22$282
This Expedia deal was found by Cheapflights users on 12/22. 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.
Fri 12/266:00 amORD - ORF
1 stop6h 39mFrontier
Wed 12/3111:44 amORF - ORD
1 stop11h 40mFrontier
Deal found 12/22$282
This Frontier deal was found by Cheapflights users on 12/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:15 amMDW - ORF
1 stop7h 12mFrontier
Wed 12/3111:44 amORF - MDW
1 stop11h 28mFrontier
Deal found 12/23$292
This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:12 amMDW - ORF
1 stop5h 57mFrontier
Wed 12/3111:44 amORF - MDW
1 stop11h 28mFrontier
Deal found 12/22$307
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:12 amMDW - ORF
1 stop9h 15mFrontier
Fri 1/22:34 pmORF - MDW
1 stop8h 38mFrontier
Deal found 12/21$367
This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - ORF
1 stop6h 27mFrontier
Fri 1/22:34 pmORF - MDW
1 stop8h 38mFrontier
Deal found 12/22$392
This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 amORD - ORF
1 stop6h 39mFrontier
Sat 12/275:47 pmORF - ORD
1 stop5h 59mFrontier
Deal found 12/22$402
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Mon 12/296:00 amORD - ORF
1 stop6h 09mFrontier
Wed 12/3111:44 amORF - ORD
1 stop11h 40mFrontier
Deal found 12/22$417
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Mon 12/296:00 amORD - ORF
1 stop6h 09mMultiple Airlines
Wed 12/313:01 pmORF - ORD
1 stop25h 01mMultiple Airlines
Deal found 12/22$419
This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:15 amMDW - ORF
1 stop7h 12mFrontier
Mon 12/292:04 pmORF - MDW
1 stop9h 08mFrontier
Deal found 12/22$427
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:10 amORD - ORF
1 stop9h 17mFrontier
Fri 1/22:34 pmORF - ORD
1 stop8h 50mFrontier
Deal found 12/21$427
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Sun 12/286:00 amORD - ORF
2 stops31h 06mMultiple Airlines
Wed 12/313:01 pmORF - ORD
1 stop25h 01mMultiple Airlines
Deal found 12/22$448

Find flight deals from Chicago to Chesapeake

Keep the following information in mind while searching for Chicago to Chesapeake flight deals. Data was last updated December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$103
(Mytrip)

One-way from

$45
(Priceline)

Popular in

April

Cheapest in

September

Average price

$380
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
Search Deals
From Chicago (CHI) to Chesapeake
Search Deals
One-way flight from Chicago (CHI) to Chesapeake
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 23, 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

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 1/9

5:15 am-6:38 pm

1 stop12h 23m

Norfolk

Mon 1/12

7:33 pm-11:22 am

1 stop16h 49m

$184

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 2/21

12:44 pm-9:50 pm

1 stop8h 06m

Norfolk

Mon 2/23

6:45 am-5:46 pm

1 stop12h 01m

$209

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 1/9

8:43 pm-1:26 pm

2 stops15h 43m

Norfolk

Mon 1/12

7:33 pm-11:22 am

1 stop16h 49m

$215

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 1/15

9:13 am-9:50 pm

2 stops11h 37m

Norfolk

Mon 1/19

11:17 am-10:19 pm

1 stop12h 02m

$232

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 1/17

8:22 am-9:50 pm

2 stops12h 28m

Norfolk

Thu 1/22

11:43 am-10:19 pm

1 stop11h 36m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 1/17

8:22 am-9:50 pm

2 stops12h 28m

Norfolk

Mon 1/19

11:17 am-12:05 pm

1 stop25h 48m

$244

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 1/8

5:15 am-6:38 pm

1 stop12h 23m

Norfolk

Sun 1/11

6:45 am-5:52 pm

1 stop12h 07m

$265

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 2/4

6:10 pm-9:32 pm

Nonstop2h 22m

Norfolk

Tue 2/10

6:13 am-9:43 am

1 stop4h 30m

$273

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/10

3:35 pm-11:27 pm

1 stop6h 52m

Norfolk

Tue 1/13

4:45 pm-6:19 pm

Nonstop2h 34m

$273

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 2/4

10:05 am-4:45 pm

1 stop5h 40m

Norfolk

Tue 2/10

6:30 am-11:40 am

1 stop6h 10m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 39 results
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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 December 19, 2025.

The best time to book flights from Chicago to Chesapeake is 68 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, February is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $121). Flying from Chicago to Chesapeake in December is currently the most expensive (average of $267). 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 23, 2025.

One of the essential ways to save on airfare from Chicago to Chesapeake is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 18% on airfare.

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 December 20, 2025.

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

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 23, 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
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,106 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,074 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $273, Spirit Airlines can have you in Chesapeake from Chicago in 2h 22m. The distance from Chicago to Chesapeake is about 715 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $93 on Frontier. Other airlines that offer cheap prices include American Airlines from $115 and United Airlines from $132 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: GoJet (73%), United Airlines (69%), Qatar Airways (65%).

  • What are the cheapest flights from Chicago to Chesapeake?

    The cheapest flight price from Chicago to Chesapeake is $119. On average you can expect to pay $390. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $103.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Chesapeake (average of $121). Flying from Chicago to Chesapeake in December is currently the most expensive (average of $267). 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

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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
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Top 4 airlines flying from Chicago to Chesapeake

Discover the top 4 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$207Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$213Average$371FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$234Average$394FlexibilityNo cancel feeOn-time71%

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