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$79+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or March, booked 88 days in advance, depart on a Wednesday or Thursday 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 junio 12, 2025.

Round-trip from

$204
(American Airlines)

One-way from

$79
(Southwest)

Popular in

December

Cheapest in

September

Average price

$387
From Chesapeake to Chicago (CHI)
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One-way flight from Chesapeake to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($15 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 June 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 junio 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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.
jue. 9/46:15 pmORF - ORD
Nonstop2h 34mAmerican Airlines
sáb. 9/611:26 amORD - ORF
1 stop4h 59mAmerican Airlines
Deal found 6/12$204
This Southwest deal was found by Cheapflights users on 6/11. 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. 9/45:30 amORF - MDW
Nonstop2h 00mSouthwest
sáb. 9/68:05 amMDW - ORF
2 stops6h 05mSouthwest
Deal found 6/11$209
This Southwest deal was found by Cheapflights users on 6/10. 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.
mar. 9/96:05 amORF - ORD
1 stop6h 45mSouthwest
mar. 9/161:50 pmORD - ORF
1 stop6h 50mSouthwest
Deal found 6/10$212
This FlightHub deal was found by Cheapflights users on 6/10. 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.
jue. 7/34:14 pmORF - ORD
1 stop8h 31mSpirit Airlines
mar. 7/85:51 amORD - ORF
1 stop5h 15mSpirit Airlines
Deal found 6/10$222
This Delta deal was found by Cheapflights users on 6/10. 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. 8/166:00 amORF - MDW
1 stop3h 35mDelta
mié. 8/209:31 amMDW - ORF
1 stop5h 52mDelta
Deal found 6/10$224
This United Airlines deal was found by Cheapflights users on 6/10. 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.
mié. 8/206:30 amORF - ORD
Nonstop2h 24mUnited Airlines
mié. 8/206:30 pmORD - ORF
Nonstop2h 22mUnited Airlines
Deal found 6/10$227
This Delta deal was found by Cheapflights users on 6/11. 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.
vie. 10/315:50 amORF - ORD
1 stop4h 35mDelta
lun. 11/310:35 amORD - ORF
1 stop6h 25mDelta
Deal found 6/11$241
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/103:54 pmORF - RFD
1 stop16h 58mMultiple Airlines
jue. 7/179:21 amRFD - ORF
2 stops31h 14mMultiple Airlines
Deal found 6/10$247
This Mytrip deal was found by Cheapflights users on 6/9. 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.
mar. 7/155:50 amORF - ORD
1 stop18h 21mMultiple Airlines
sáb. 7/195:38 pmORD - ORF
1 stop13h 37mMultiple Airlines
Deal found 6/9$249
This CheapOair deal was found by Cheapflights users on 6/10. 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.
jue. 10/169:48 amORF - MDW
1 stop22h 56mFrontier
dom. 10/198:39 amMDW - ORF
1 stop5h 43mFrontier
Deal found 6/10$253
This Booking.com deal was found by Cheapflights users on 6/11. 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.
vie. 9/266:32 pmORF - ORD
1 stop27h 02mFrontier
dom. 10/266:10 amORD - ORF
1 stop8h 12mFrontier
Deal found 6/11$316
This Mytrip deal was found by Cheapflights users on 6/11. 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.
jue. 6/263:55 pmORF - RFD
1 stop17h 00mAllegiant Air
mar. 7/111:12 amRFD - ORF
2 stops27h 33mAllegiant Air
Deal found 6/11$392

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 junio 12, 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 - MDW

ORFMDW

Norfolk

jue. 9/4

5:30 am-6:30 am

Nonstop2h 00m

Chicago Midway

sáb. 9/6

8:05 am-3:10 pm

2 stops6h 05m

$209

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

vie. 10/31

7:30 am-9:00 am

Nonstop2h 30m

Chicago O'Hare Intl

lun. 11/3

6:30 pm-9:53 pm

Nonstop2h 23m

$211

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mar. 9/9

6:05 am-11:50 am

1 stop6h 45m

Chicago O'Hare Intl

mar. 9/16

1:50 pm-9:40 pm

1 stop6h 50m

$212

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

jue. 7/3

4:14 pm-11:45 pm

1 stop8h 31m

Chicago O'Hare Intl

mar. 7/8

5:51 am-12:06 pm

1 stop5h 15m

$222

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

sáb. 8/16

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

mié. 8/20

9:31 am-4:23 pm

1 stop5h 52m

$224

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 8/20

6:30 am-7:54 am

Nonstop2h 24m

Chicago O'Hare Intl

mié. 8/20

6:30 pm-9:52 pm

Nonstop2h 22m

$227

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

vie. 10/31

5:50 am-9:25 am

1 stop4h 35m

Chicago O'Hare Intl

lun. 11/3

10:35 am-6:00 pm

1 stop6h 25m

$241

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

jue. 7/10

3:54 pm-7:52 am

1 stop16h 58m

Chicago Greater Rockford

jue. 7/17

9:21 am-5:35 pm

2 stops31h 14m

$247

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mar. 7/15

5:50 am-11:11 pm

1 stop18h 21m

Chicago O'Hare Intl

sáb. 7/19

5:38 pm-8:15 am

1 stop13h 37m

$249

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

jue. 10/16

9:48 am-7:44 am

1 stop22h 56m

Chicago Midway

dom. 10/19

8:39 am-3:22 pm

1 stop5h 43m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 27 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.

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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Chicago, you should look to book at least 88 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 junio 12, 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 June 8, 2025.

Travelers seeking maximum savings on their Chesapeake to Chicago flight should consider departing on Tuesday at noon 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 junio 12, 2025.

The most flights from C6E to CHI are scheduled on a Thursday (27 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 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 junio 12, 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
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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?

    $79 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $79 and $84, 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: Japan Airlines (93%), Avianca (90%), ANA (80%).

  • What are the cheapest flights from Chesapeake to Chicago?

    Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $1,169, our data indicates the cheapest price to be $139. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $157.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 6 airlines flying from Chesapeake to Chicago

Discover the top 6 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$251FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$443FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$177Average$389FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$251Average$385FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%

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