$89+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
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 February, 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 April 24, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $288 (Delta) |
One-way from | $89 (Frontier) |
Popular in | July |
Cheapest in | September |
Average price | $397 |
Find flight deals from Chicago to Chesapeake
Cheapest flights from Chicago to ChesapeakeExplore 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 April 24, 2025.
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 April 24, 2025.
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight 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 April 24, 2025.
Use the filters below to find and compare flights from Chicago to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Fri 6/20
7:39 pm-9:26 am
1 stop12h 47m
Norfolk
Sun 6/22
12:53 pm-12:24 am
1 stop12h 31m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 5/20
6:25 pm-11:24 pm
1 stop3h 59m
Norfolk
Tue 5/27
6:00 am-8:40 am
1 stop3h 40m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 4/26
4:30 pm-10:32 am
1 stop17h 02m
Norfolk
Mon 4/28
4:05 pm-11:09 pm
1 stop8h 04m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 5/23
6:35 am-4:27 pm
1 stop8h 52m
Norfolk
Mon 5/26
5:12 pm-10:14 pm
1 stop6h 02m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sun 5/11
5:05 am-2:16 pm
1 stop8h 11m
Norfolk
Sat 5/17
12:13 pm-11:29 pm
1 stop12h 16m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/28
5:00 am-11:25 am
1 stop5h 25m
Norfolk
Sun 8/31
6:00 pm-7:10 pm
Nonstop2h 10m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 5/17
6:43 pm-10:10 pm
Nonstop2h 27m
Norfolk
Tue 5/20
7:00 am-8:23 am
Nonstop2h 23m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 5/24
11:10 am-2:29 pm
Nonstop2h 19m
Norfolk
Sun 5/25
6:30 am-7:55 am
Nonstop2h 25m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Fri 6/6
3:57 pm-11:10 pm
1 stop6h 13m
Norfolk
Tue 6/10
10:09 am-2:30 pm
1 stop5h 21m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sun 6/8
11:45 am-8:59 pm
2 stops32h 14m
Norfolk
Sun 6/15
11:35 am-7:46 pm
2 stops33h 11m
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.
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 April 18, 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 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 April 24, 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 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 April 24, 2025.
The most flights from CHI to C6E are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 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 April 24, 2025.
To help decide which airline to fly from Chicago to Chesapeake, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Crew
Comfort
Boarding
Entertainment
Overall
Reviews
Gina,Apr 2025
LAS - DEN
Food
Crew
Comfort
Boarding
Entertainment
Overall
Reviews
Gina,Apr 2025
LAS - DEN
Food
Crew
Comfort
Boarding
Entertainment
Overall
Reviews
Gina,Apr 2025
LAS - DEN
Food
Crew
Comfort
Boarding
Entertainment
Overall
Reviews
Gina,Apr 2025
LAS - DEN
Food
Crew
Comfort
Boarding
Entertainment
Overall
Reviews
Gina,Apr 2025
LAS - DEN
Food
Crew
Comfort
Boarding
Entertainment
Overall
Reviews
Gina,Apr 2025
LAS - DEN
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.
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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.
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 April 24, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$245 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$167 | Average$389 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$200 | Average$372 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$415 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$346 | Average$553 | FlexibilityNo cancel fee | On-timeN/A |