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$58+ Cheap flights from Chesapeake, VA to Chicago (CHI)

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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
nov. 9 — nov. 161
1 adult
sáb. 11/9
sáb. 11/16
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The best prices from Chesapeake to Chicago are usually found in March or January, booked 36 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Chesapeake to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Chicago (CHI). 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 noviembre 4, 2024.

Popular in

June

Cheapest in

March

Round-trip from

$128
(Frontier)

One-way from

$60
(Frontier)
High demand for flights, 11% potential price rise
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Best time to find cheap flights, 13% potential price drop
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From Chesapeake to Chicago (CHI)
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One-way flight from Chesapeake to Chicago (CHI)
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Find flight deals from Chesapeake to Chicago

Cheapest flights from Chesapeake to Chicago
Explore the most affordable flight options available from Chesapeake to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 4, 2024.

This FareScan deal was found by Cheapflights users on 11/3. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/133:55 pmORF - ORD
1 stop29h 20mSpirit Airlines
dom. 11/1710:21 amORD - ORF
2 stops31h 50mSpirit Airlines
Deal found 11/3$254
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/65:45 amORF - ORD
3 stops19h 48mMultiple Airlines
dom. 12/86:20 amORD - ORF
2 stops37h 04mMultiple Airlines
Deal found 11/3$269
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/69:19 pmORF - MDW
2 stops27h 10mMultiple Airlines
dom. 12/85:15 amMDW - ORF
2 stops16h 50mMultiple Airlines
Deal found 11/3$283
This United Airlines deal was found by Cheapflights users on 11/4. 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.
sáb. 11/168:00 pmORF - ORD
2 stops13h 02mUnited Airlines
dom. 11/1711:05 amORD - ORF
Nonstop2h 12mUnited Airlines
Deal found 11/4$298
This Delta deal was found by Cheapflights users on 11/4. 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.
mié. 12/46:00 amORF - ORD
1 stop13h 26mDelta
mar. 12/108:40 amORD - ORF
1 stop12h 56mDelta
Deal found 11/4$315
This Delta deal was found by Cheapflights users on 11/3. 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.
sáb. 11/235:50 amORF - MDW
1 stop4h 00mDelta
dom. 11/245:42 pmMDW - ORF
1 stop4h 21mDelta
Deal found 11/3$323
This Southwest deal was found by Cheapflights users on 11/3. 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.
jue. 11/286:00 amORF - MDW
Nonstop2h 15mSouthwest
mar. 12/36:20 pmMDW - ORF
Nonstop1h 55mSouthwest
Deal found 11/3$341
This American Airlines deal was found by Cheapflights users on 11/3. 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.
mar. 11/266:50 amORF - ORD
Nonstop2h 27mAmerican Airlines
mar. 12/38:30 pmORD - ORF
Nonstop2h 15mAmerican Airlines
Deal found 11/3$344
This Frontier deal was found by Cheapflights users on 11/3. 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.
jue. 12/191:42 pmORF - MDW
1 stop7h 00mFrontier
dom. 12/2212:58 pmMDW - ORF
1 stop6h 03mFrontier
Deal found 11/3$348
This Southwest deal was found by Cheapflights users on 11/3. 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.
jue. 11/285:35 amORF - ORD
1 stop7h 15mSouthwest
mar. 12/311:25 amORD - ORF
2 stops9h 25mSouthwest
Deal found 11/3$364
This Mytrip deal was found by Cheapflights users on 11/3. 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.
vie. 11/86:30 amORF - RFD
1 stop12h 45mMultiple Airlines
dom. 11/109:16 pmRFD - ORF
2 stops22h 38mMultiple Airlines
Deal found 11/3$773

Find flights from Chesapeake to Chicago within your budget

Customize your flight search to find flights from Chesapeake to Chicago 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 2,455,398 searches. Data last updated noviembre 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

lun. 2/10

3:42 pm-11:47 pm

1 stop9h 05m

$58

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mar. 12/10

5:45 am-4:06 pm

1 stop11h 21m

$61

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

dom. 2/2

12:24 pm-6:57 pm

1 stop7h 33m

$113

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

lun. 1/20

3:42 pm-11:24 pm

1 stop8h 42m

$60

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mar. 12/24

11:20 am-1:00 pm

Nonstop2h 40m

$153

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

mié. 1/1

8:00 am-2:34 pm

1 stop7h 34m

$162

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

mié. 1/1

10:30 am-5:05 pm

2 stops7h 35m

$167

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

vie. 12/27

7:00 am-8:35 am

Nonstop2h 35m

$199

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 1/1

12:29 pm-7:14 pm

1 stop7h 45m

$162

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mar. 12/24

1:00 pm-10:00 pm

2 stops10h 00m

$167

Flights are sorted by cheapest first

Deals found on 11/4

Showing 1-10 of 25 results
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Best time to book a flight from Chesapeake to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Chesapeake 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 Chesapeake to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Chicago. Price data was last updated on November 1, 2024.

To ensure you get the cheapest price possible for a flight from Chesapeake to Chicago, you should look to book at least 36 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, September is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $232). Flying from Chesapeake to Chicago in June is currently the most expensive (average of $308). 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 C6E to CHI?

Find hourly flight availability from Chesapeake to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 4, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Chicago as you normally would.

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

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Chicago. Price data was last updated on October 27, 2024.

Travelers seeking maximum savings on their Chesapeake to Chicago flight should consider departing on Monday evenings 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.

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Weekly flight availability from Chesapeake to Chicago

Explore weekly flight availability from Chesapeake to Chicago. 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 noviembre 4, 2024.

The most flights from C6E to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated noviembre 4, 2024.
Get a feel of what it's like to fly with Delta, American Airlines and Spirit Airlines from Chesapeake to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,089 reviews

Crew

8.7

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Crew

8.7

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Crew

8.7

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Crew

8.7

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,803 reviews
Southwest
8.1
Very good
5,089 reviews

Crew

8.7

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,089 reviews

Crew

8.7

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

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

  • Can I find flights from Chesapeake to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Chesapeake to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $128, but on average you can expect to pay $262.

  • Are there nonstop flights from Chesapeake to Chicago for under $400 on Cheapflights?

    Cheapflights has at least 3 direct flights from Chesapeake to Chicago under $400. A good price for a nonstop flight from Chesapeake to Chicago is less than $351.

  • Are there last-minute flights available from Chesapeake to Chicago for under $200?

    There are currently 8+ open flights from Chesapeake to Chicago within the next 7 days for less than $200.

  • What days are nonstop flights available from Chesapeake to Chicago?

    Days when nonstop flights are available for this flight are: Monday.

  • How many flights depart from Chesapeake to Chicago on average per day?

    On average 6 flights depart from Chesapeake to Chicago per day.
    Morning (6am - Noon) - 100% of flight departures

  • How long is the flight from Chesapeake to Chicago?

    Frontier, Spirit Airlines, and United Airlines can get you from Chesapeake to Chicago in just under 8h 14m. Your travel time can differ by up to 20h 38m. There are 644 mi between Chesapeake and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $60 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $61 and $153, respectively.

  • What are the most popular routes from Chesapeake to Chicago?

    When deciding which route to take from Chesapeake to Chicago consider Norfolk - Chicago O'Hare Intl, Norfolk - Chicago Midway or Norfolk - Chicago Greater Rockford as they are the most popular.

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

    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 Chesapeake to Chicago on time: Avianca (100%), Republic Airways (98%), ANA (98%).

  • What are the cheapest flights from Chesapeake to Chicago?

    Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $1,188, our data indicates the cheapest price to be $159. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $177.

  • What does RIC to ORD mean?

    Richmond Byrd Intl Airport is RIC and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Chesapeake to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Chesapeake to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chesapeake to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chesapeake to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

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

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

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

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

  • Can I find deals for flights from Chesapeake to Chicago that allow pets onboard?

    Many airlines flying from Chesapeake to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chesapeake to Chicago?

    Yes, you can often find last-minute deals on Chesapeake to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chesapeake to Chicago flight deals updated?

    The Chesapeake to Chicago flight deals you see on this page were last updated on 11/4.

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

    Currently, September is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $232). Flying from Chesapeake to Chicago in June is currently the most expensive (average of $308). 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 Chesapeake to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
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Reagan-National to Champaign flights
Richmond to Rockford flights
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Blountville to Midway flights

Top 5 airlines flying from Chesapeake to Chicago

Discover the top 5 airlines that operate flights from Chesapeake to Chicago. 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 2,455,398 searches. Data last updated noviembre 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$179FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$392FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$188Average$390FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$199Average$340FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$220Average$370FlexibilityNo cancel feeOn-time71%
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