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$54+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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The best prices from Chesapeake to Chicago are usually found in March or February, booked 36 days in advance, depart on a Wednesday or Saturday 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 December 23, 2024.

Round-trip from

$267
(American Airlines)

One-way from

$54
(Mytrip)

Popular in

June

Cheapest in

March

Average price

$384
From Chesapeake to Chicago (CHI)
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One-way flight from Chesapeake to Chicago (CHI)
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High demand for flights, 3% potential price rise
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Best time to find cheap flights, 0% potential price drop
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Average for round-trip flights in December 2024
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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 December 23, 2024.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:00 amORF - ORD
Nonstop2h 35mAmerican Airlines
Mon 1/135:50 pmORD - ORF
Nonstop2h 04mAmerican Airlines
Deal found 12/22$296
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/263:20 pmORF - ORD
1 stop6h 30mMultiple Airlines
Tue 1/78:14 pmORD - ORF
1 stop11h 36mMultiple Airlines
Deal found 12/22$300
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3112:35 pmORF - MDW
1 stop7h 15mSouthwest
Mon 1/136:05 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 12/22$328
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/314:40 pmORF - ORD
1 stop6h 20mSouthwest
Mon 1/1311:25 amORD - ORF
2 stops9h 25mSouthwest
Deal found 12/22$342
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/293:26 pmORF - ORD
1 stop6h 43mFrontier
Mon 1/278:38 amORD - ORF
1 stop5h 18mFrontier
Deal found 12/23$363
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:00 amORF - ORD
1 stop4h 55mUnited Airlines
Wed 1/810:48 amORD - ORF
2 stops11h 38mUnited Airlines
Deal found 12/21$562
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 12/305:29 amORF - MDW
1 stop4h 54mDelta
Wed 1/85:07 pmMDW - ORF
1 stop4h 14mDelta
Deal found 12/21$572
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/261:42 pmORF - MDW
1 stop20h 49mFrontier
Sun 12/2912:58 pmMDW - ORF
1 stop6h 03mFrontier
Deal found 12/22$905
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/269:45 amORF - ORD
2 stops23h 52mSpirit Airlines
Tue 1/79:35 pmORD - ORF
2 stops24h 40mSpirit Airlines
Deal found 12/22$1,048
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2612:29 pmORF - ORD
2 stops9h 30mDelta
Mon 12/305:40 amORD - ORF
1 stop4h 44mDelta
Deal found 12/22$1,100

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 2,558,603 searches. Data last updated December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 1/27

5:47 am-10:47 am

1 stop6h 00m

Chicago O'Hare Intl

Tue 1/28

5:50 pm-8:54 pm

Nonstop2h 04m

$267

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/23

5:25 am-11:20 am

1 stop6h 55m

Chicago O'Hare Intl

Sun 1/26

5:35 am-8:34 am

2 stops25h 59m

$268

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 1/7

6:00 am-4:06 pm

1 stop11h 06m

Chicago O'Hare Intl

Fri 1/10

3:56 pm-3:36 pm

1 stop22h 40m

$276

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/9

4:42 pm-6:23 pm

Nonstop2h 41m

Chicago O'Hare Intl

Sat 1/11

6:20 pm-9:30 pm

Nonstop2h 10m

$277

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 1/23

7:15 am-8:35 am

Nonstop2h 20m

Chicago Midway

Mon 1/27

6:05 pm-9:05 pm

Nonstop2h 00m

$278

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 1/9

5:30 am-10:12 am

1 stop5h 42m

Chicago Midway

Mon 1/13

5:07 pm-11:59 pm

1 stop5h 52m

$296

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/23

6:50 pm-10:20 pm

1 stop4h 30m

Chicago O'Hare Intl

Mon 1/27

11:25 am-9:50 pm

2 stops9h 25m

$301

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sun 3/9

7:25 am-12:40 pm

1 stop6h 15m

Chicago O'Hare Intl

Sun 3/23

5:00 pm-11:02 pm

1 stop5h 02m

$416

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/2

3:20 pm-8:50 pm

1 stop6h 30m

Chicago O'Hare Intl

Sun 1/5

11:24 am-8:01 pm

1 stop7h 37m

$503

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 1/27

3:46 pm-10:27 pm

1 stop7h 41m

$54

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 21 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 December 20, 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.

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

Currently, August is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $245). Flying from Chesapeake to Chicago in March is currently the most expensive (average of $317). 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 December 23, 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 December 16, 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.

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 December 23, 2024.

The most flights from C6E to CHI are scheduled on a Friday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 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 December 23, 2024.
Get a feel of what it's like to fly with Frontier, United Airlines and American 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
4,780 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

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
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

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
4,780 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

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
9,022 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

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
4,780 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

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
8,113 reviews
Southwest
8.1
Very good
4,780 reviews

Overall

8.1

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

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 Chesapeake to Chicago. 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 Chesapeake to Chicago one-way?

    $54 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 Southwest, with prices starting from $91 and $119, 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: Envoy Air (96%), ANA (95%), Avianca (90%).

  • What are the cheapest flights from Chesapeake to Chicago?

    Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $906, our data indicates the cheapest price to be $185. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $171.

  • 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.

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

    Currently, August is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $245). Flying from Chesapeake to Chicago in March is currently the most expensive (average of $317). 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.

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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.
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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 2,558,603 searches. Data last updated December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$387FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$248Average$385FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$391FlexibilityNo cancel feeOn-time63%
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