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$89+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in March or September, booked 70 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Chesapeake to Chicago

Keep the following information in mind while searching for Chesapeake to Chicago flight deals. Data was last updated April 24, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$210
(Mytrip)

One-way from

$89
(Frontier)

Popular in

December

Cheapest in

March

Average price

$387
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
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From Chesapeake to Chicago (CHI)
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One-way flight from Chesapeake to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 24, 2025.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/163:49 pmORF - ORD
1 stop8h 22mFrontier
Mon 5/196:20 amORD - ORF
1 stop7h 36mFrontier
Deal found 4/22$208
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.
Fri 5/303:19 pmORF - RFD
1 stop17h 47mAllegiant Air
Wed 6/49:35 amRFD - ORF
1 stop28h 25mAllegiant Air
Deal found 4/23$210
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.
Sat 5/1712:13 pmORF - ORD
1 stop12h 16mMultiple Airlines
Mon 5/196:20 amORD - ORF
1 stop7h 36mMultiple Airlines
Deal found 4/23$225
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/235:12 pmORF - MDW
1 stop6h 02mFrontier
Sat 5/316:10 amMDW - ORF
1 stop9h 17mFrontier
Deal found 4/23$250
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1512:13 pmORF - ORD
1 stop8h 50mSpirit Airlines
Sun 5/187:47 amORD - ORF
1 stop25h 42mSpirit Airlines
Deal found 4/22$255
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:15 amORF - ORD
Nonstop2h 27mUnited Airlines
Tue 5/276:20 pmORD - ORF
Nonstop2h 18mUnited Airlines
Deal found 4/23$271
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.
Sat 5/2410:52 amORF - ORD
1 stop7h 34mAmerican Airlines
Wed 5/286:43 pmORD - ORF
Nonstop2h 27mAmerican Airlines
Deal found 4/23$275
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.
Tue 7/15:23 amORF - MDW
1 stop5h 18mDelta
Sat 7/54:26 pmMDW - ORF
1 stop6h 58mDelta
Deal found 4/23$285
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.
Wed 5/216:15 amORF - MDW
Nonstop2h 10mSouthwest
Tue 5/276:35 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 4/23$288
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.
Fri 5/233:19 pmORF - RFD
1 stop17h 37mMultiple Airlines
Sun 6/14:16 pmRFD - ORF
3 stops24h 07mMultiple Airlines
Deal found 4/23$303
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.
Wed 6/46:40 amORF - ORD
1 stop6h 10mSouthwest
Sun 6/86:00 amORD - ORF
1 stop7h 40mSouthwest
Deal found 4/22$343
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.
Wed 6/48:00 amORF - ORD
1 stop5h 20mDelta
Fri 6/63:57 pmORD - ORF
1 stop6h 13mDelta
Deal found 4/22$352

Cheapflights Fare Finder

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 April 24, 2025.
Use the filters below to find and compare flights from Chesapeake to Chicago that are best for you.

Fly from

Chesapeake

Fly to

Chicago

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 5/16

3:49 pm-11:11 pm

1 stop8h 22m

Chicago O'Hare Intl

Mon 5/19

6:20 am-2:56 pm

1 stop7h 36m

$208

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Fri 5/30

3:19 pm-8:06 am

1 stop17h 47m

Chicago Greater Rockford

Wed 6/4

9:35 am-3:00 pm

1 stop28h 25m

$210

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 5/17

12:13 pm-11:29 pm

1 stop12h 16m

Chicago O'Hare Intl

Mon 5/19

6:20 am-2:56 pm

1 stop7h 36m

$221

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 5/23

5:12 pm-10:14 pm

1 stop6h 02m

Chicago Midway

Wed 5/28

6:40 am-4:27 pm

1 stop8h 47m

$250

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 5/15

12:13 pm-8:03 pm

1 stop8h 50m

Chicago O'Hare Intl

Sun 5/18

7:47 am-10:29 am

1 stop25h 42m

$255

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 5/24

10:52 am-5:26 pm

1 stop7h 34m

Chicago O'Hare Intl

Wed 5/28

6:43 pm-10:10 pm

Nonstop2h 27m

$275

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 7/1

5:23 am-9:41 am

1 stop5h 18m

Chicago Midway

Sat 7/5

4:26 pm-12:24 am

1 stop6h 58m

$285

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 6/9

5:40 am-6:45 am

Nonstop2h 05m

Chicago Midway

Tue 6/10

7:15 am-1:20 pm

1 stop5h 05m

$298

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 6/18

5:05 pm-6:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

Mon 6/23

6:20 pm-9:38 pm

Nonstop2h 18m

$305

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 9/5

7:50 pm-11:55 pm

1 stop5h 05m

Chicago O'Hare Intl

Sun 9/7

6:00 am-12:53 pm

1 stop5h 53m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 27 results
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2
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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.

Cheapflights Insights

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

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 April 18, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Chicago, you should look to book at least 70 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 $321). 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 April 24, 2025.

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 March 30, 2025.

Travelers seeking maximum savings on their Chesapeake to Chicago flight should consider departing on Thursday afternoons 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 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 April 24, 2025.

The most flights from C6E to CHI 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 (20 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 April 24, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United 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
8.0
Very good
4,286 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $89 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 $109 and $133, 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: ANA (75%), Qatar Airways (74%), Royal Jordanian (73%).

  • What are the cheapest flights from Chesapeake to Chicago?

    Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $740, our data indicates the cheapest price to be $139. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $181.

  • 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 $321). 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

Traveling to a place near Chesapeake?

Book flights to Chesapeake if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$230FlexibilityNo cancel feeOn-time65%
DeltaCheapest$176Average$474FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$186Average$391FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$251Average$395FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$381FlexibilityNo cancel feeOn-time63%

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