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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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or March, booked 10 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 July 31, 2025.

Round-trip from

$235
(FlightHub)

One-way from

$79
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$375
From Chesapeake to Chicago (CHI)
Search Deals
One-way flight from Chesapeake to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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 10/165:24 amORF - ORD
1 stop6h 19mSpirit Airlines
Thu 10/236:30 amORD - ORF
1 stop9h 13mSpirit Airlines
Deal found 7/31$235
This Delta deal was found by Cheapflights users on 7/31. 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 8/276:00 amORF - MDW
1 stop3h 35mDelta
Wed 9/34:25 pmMDW - ORF
1 stop6h 59mDelta
Deal found 7/31$237
This Delta deal was found by Cheapflights users on 7/30. 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 10/141:35 pmORF - ORD
1 stop6h 14mDelta
Tue 10/2110:35 amORD - ORF
1 stop6h 25mDelta
Deal found 7/30$237
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 9/46:15 pmORF - MDW
Nonstop2h 05mSouthwest
Tue 9/96:20 pmMDW - ORF
Nonstop2h 05mSouthwest
Deal found 7/30$239
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 9/86:14 pmORF - ORD
Nonstop2h 34mAmerican Airlines
Wed 9/107:34 pmORD - ORF
Nonstop2h 22mAmerican Airlines
Deal found 7/31$239
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/89:45 amORF - ORD
1 stop4h 00mSouthwest
Wed 9/106:00 amORD - ORF
2 stops8h 00mSouthwest
Deal found 7/31$242
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/256:30 amORF - ORD
Nonstop2h 25mUnited Airlines
Tue 9/304:00 pmORD - ORF
1 stop6h 30mUnited Airlines
Deal found 7/31$245
This Mytrip deal was found by Cheapflights users on 7/30. 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 8/89:52 pmORF - RFD
2 stops19h 43mMultiple Airlines
Sun 8/109:21 amRFD - ORF
3 stops28h 04mMultiple Airlines
Deal found 7/30$488

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 July 31, 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

Thu 10/16

5:24 am-10:43 am

1 stop6h 19m

Chicago O'Hare Intl

Thu 10/23

6:30 am-4:43 pm

1 stop9h 13m

$235

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 8/27

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Wed 9/3

4:25 pm-12:24 am

1 stop6h 59m

$237

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 10/14

5:07 pm-8:23 pm

1 stop4h 16m

Chicago O'Hare Intl

Wed 10/15

6:45 am-12:30 pm

1 stop4h 45m

$237

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 9/4

6:15 pm-7:20 pm

Nonstop2h 05m

Chicago Midway

Tue 9/9

6:20 pm-9:25 pm

Nonstop2h 05m

$239

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 9/8

6:14 pm-7:48 pm

Nonstop2h 34m

Chicago O'Hare Intl

Wed 9/10

7:34 pm-10:56 pm

Nonstop2h 22m

$239

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 9/8

9:45 am-12:45 pm

1 stop4h 00m

Chicago O'Hare Intl

Wed 9/10

6:00 am-3:00 pm

2 stops8h 00m

$242

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 9/25

6:30 am-7:55 am

Nonstop2h 25m

Chicago O'Hare Intl

Tue 9/30

4:00 pm-11:30 pm

1 stop6h 30m

$245

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Fri 8/8

9:52 pm-4:35 pm

2 stops19h 43m

Chicago Greater Rockford

Sun 8/10

9:21 am-2:25 pm

3 stops28h 04m

$488

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 9/6

5:20 am-5:39 pm

1 stop13h 19m

$79

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 10/8

3:27 pm-10:58 pm

1 stop8h 31m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 20 results
1
2

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 July 25, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Chicago, you should look to book at least 10 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 July 31, 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 July 27, 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 July 31, 2025.

The most flights from C6E to CHI are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from Chesapeake to Chicago?

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 July 31, 2025.
Read through reviews of airlines operating flights from Chesapeake to Chicago, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,049 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Spirit Airlines. You may also be able to find cheap deals on Frontier and Southwest, with prices starting from $95 and $109, 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 (93%), Piedmont Airlines (85%), ANA (84%).

  • What are the cheapest flights from Chesapeake to Chicago?

    Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $1,233, our data indicates the cheapest price to be $90. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $178.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$449FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$191Average$390FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$383FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$231Average$374FlexibilityNo cancel feeOn-time63%

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