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

$90 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 Allegiant Air, with prices starting from $99 and $105, 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 cheapest flights from Chesapeake to Chicago?

Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $1,555, our data indicates the cheapest price to be $138. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $192.

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: Qatar Airways (79%), ANA (79%), Royal Jordanian (76%).

What are the most popular airlines that fly from Chesapeake to Chicago?

The most popular airlines flying from Chesapeake to Chicago are American Airlines, Delta and Spirit Airlines. Something to consider prior to booking your flight.

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

Users have found that booking a flight from Chesapeake to Chicago at least 11 days early can save you up to 95% on average compared to booking a flight this week. If booking 11 days before your flight isn’t an option for you, users have found flights from Chesapeake to Chicago for as little as $148 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $586 for flights departing within the next 3 days.

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

September can be a great time to fly to Chicago from Chesapeake with a flight ticket averaging about $372. Cheapflights users have found deals in the month of September for as cheap as $121. The most expensive prices can be found in the month of June.

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.

$86+ Flights from Chesapeake to Chicago

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or April, booked 10 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Chesapeake to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$233 (Mytrip)
One-way from	$90 (FlightHub)
Popular in	June
Cheapest in	September
Average price	$357

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)

Search Deals

One-way flight from Chesapeake to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 2% potential increase in price ($9 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 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 abril 3, 2025.

ter 4/296:00 amORF - ORD

1 stop28h 24mSpirit Airlines

ter 5/611:47 amORD - ORF

1 stop21h 42mSpirit Airlines

Deal found 4/1

$233

sáb 5/2412:13 pmORF - ORD

1 stop8h 50mMultiple Airlines

dom 5/257:47 amORD - ORF

1 stop24h 49mMultiple Airlines

Deal found 4/1

$237

qui 4/1710:09 amORF - MDW

1 stop8h 22mFrontier

dom 4/2012:46 pmMDW - ORF

1 stop27h 12mFrontier

Deal found 4/2

$240

qui 4/175:41 pmORF - ORD

1 stop16h 08mFrontier

qui 4/244:30 pmORD - ORF

1 stop26h 02mFrontier

Deal found 4/1

$240

ter 6/105:25 amORF - MDW

Nonstop2h 05mSouthwest

qua 6/117:00 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 4/2

$271

ter 6/105:05 pmORF - ORD

Nonstop2h 25mUnited Airlines

qua 6/1111:10 amORD - ORF

Nonstop2h 19mUnited Airlines

Deal found 4/1

$271

qua 8/275:55 pmORF - ORD

Nonstop2h 40mAmerican Airlines

dom 8/312:04 pmORD - ORF

Nonstop2h 21mAmerican Airlines

Deal found 4/1

$285

qua 5/215:35 amORF - MDW

1 stop5h 05mDelta

sáb 5/244:15 pmMDW - ORF

1 stop6h 10mDelta

Deal found 4/2

$288

ter 4/228:00 amORF - ORD

1 stop5h 05mDelta

qua 4/305:30 amORD - ORF

1 stop5h 49mDelta

Deal found 4/1

$291

ter 6/106:10 amORF - ORD

1 stop6h 40mSouthwest

qua 6/1111:25 amORD - ORF

2 stops10h 10mSouthwest

Deal found 4/1

$313

Best flights from Chesapeake to Chicago
Discover carefully curated flight deals from Chesapeake to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated abril 3, 2025.

ter 4/296:00 amORF - ORD

1 stop28h 24mSpirit Airlines

ter 5/611:47 amORD - ORF

1 stop21h 42mSpirit Airlines

Deal found 4/1

$233

sáb 5/2412:13 pmORF - ORD

1 stop8h 50mMultiple Airlines

dom 5/257:47 amORD - ORF

1 stop24h 49mMultiple Airlines

Deal found 4/1

$237

sáb 5/315:12 pmORF - MDW

1 stop6h 05mFrontier

qua 6/46:40 amMDW - ORF

1 stop8h 36mFrontier

Deal found 4/1

$240

ter 6/107:25 pmORF - MDW

Nonstop2h 10mSouthwest

qua 6/117:00 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 4/1

$271

ter 6/105:05 pmORF - ORD

Nonstop2h 25mUnited Airlines

qua 6/1111:10 amORD - ORF

Nonstop2h 19mUnited Airlines

Deal found 4/1

$271

sáb 5/243:10 pmORF - MDW

1 stop7h 03mDelta

dom 5/2512:48 pmMDW - ORF

1 stop4h 47mDelta

Deal found 4/1

$285

qua 8/275:55 pmORF - ORD

Nonstop2h 40mAmerican Airlines

dom 8/312:04 pmORD - ORF

Nonstop2h 21mAmerican Airlines

Deal found 4/1

$285

qui 4/175:41 pmORF - ORD

1 stop16h 08mFrontier

qui 4/244:30 pmORD - ORF

1 stop26h 02mFrontier

Deal found 4/1

$240

ter 4/228:00 amORF - ORD

1 stop5h 05mDelta

qua 4/305:30 amORD - ORF

1 stop5h 49mDelta

Deal found 4/1

$291

ter 6/106:10 amORF - ORD

1 stop6h 40mSouthwest

qua 6/1111:25 amORD - ORF

2 stops10h 10mSouthwest

Deal found 4/1

$313

qui 6/269:05 amORF - MDW

2 stops25h 39mMultiple Airlines

sex 7/2510:31 amMDW - ORF

2 stops31h 18mMultiple Airlines

Deal found 3/31

$451

Last-minute flights from Chesapeake to Chicago
Discover last-minute flight deals from Chesapeake to Chicago. Data last updated abril 3, 2025 and is based on user searches.

qua 4/96:13 pmORF - ORD

1 stop7h 07mSpirit Airlines

sáb 4/1211:45 amORD - ORF

1 stop6h 55mSpirit Airlines

Deal found 4/2

$280

qua 4/96:13 pmORF - ORD

1 stop7h 07mMultiple Airlines

seg 4/149:50 amORD - ORF

1 stop6h 08mMultiple Airlines

Deal found 4/1

$301

qui 4/105:31 pmORF - MDW

1 stop27h 24mFrontier

dom 4/1312:46 pmMDW - ORF

1 stop27h 12mFrontier

Deal found 4/2

$250

qui 4/105:31 pmORF - ORD

1 stop16h 18mFrontier

dom 4/139:25 amORD - ORF

1 stop6h 12mFrontier

Deal found 4/2

$250

qui 4/105:40 amORF - MDW

Nonstop2h 05mSouthwest

qui 4/171:20 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 4/2

$509

sex 4/115:49 amORF - ORD

1 stop5h 48mAmerican Airlines

ter 4/156:44 pmORD - ORF

Nonstop2h 14mAmerican Airlines

Deal found 4/1

$554

sex 4/117:25 amORF - MDW

1 stop6h 10mDelta

seg 4/144:59 pmMDW - ORF

1 stop4h 31mDelta

Deal found 4/1

$760

sáb 4/126:10 amORF - ORD

2 stops13h 00mUnited Airlines

ter 4/154:00 pmORD - ORF

2 stops16h 21mUnited Airlines

Deal found 4/2

$541

sáb 4/128:00 amORF - ORD

1 stop6h 45mDelta

sáb 4/196:45 amORD - ORF

2 stops7h 44mDelta

Deal found 4/1

$881

qui 4/1710:09 amORF - MDW

1 stop8h 22mFrontier

dom 4/2012:46 pmMDW - ORF

1 stop27h 12mFrontier

Deal found 4/2

$240

qui 4/175:41 pmORF - ORD

1 stop16h 08mFrontier

qui 4/244:30 pmORD - ORF

1 stop26h 02mFrontier

Deal found 4/1

$240

ter 4/228:00 amORF - ORD

1 stop5h 05mDelta

qua 4/305:30 amORD - ORF

1 stop5h 49mDelta

Deal found 4/1

$291

One-way flights from Chesapeake to Chicago
Search for one-way flight options from Chesapeake to Chicago. Find affordable one-way fares based on user searches. Data last updated abril 3, 2025.

ter 5/1312:13 pmORF - ORD

1 stop8h 50mSpirit Airlines

Deal found 4/1

$90

qui 5/84:48 pmORF - MDW

1 stop7h 51mFrontier

Deal found 4/1

$99

sex 4/254:05 pmORF - ORD

1 stop8h 03mFrontier

Deal found 4/1

$99

sex 5/233:19 pmORF - RFD

1 stop17h 37mAllegiant Air

Deal found 4/2

$105

sáb 5/246:30 pmORF - MDW

Nonstop2h 10mSouthwest

Deal found 4/1

$133

sáb 5/245:08 pmORF - ORD

Nonstop2h 25mUnited Airlines

Deal found 4/1

$133

dom 5/255:35 amORF - MDW

1 stop5h 05mDelta

Deal found 4/1

$143

qua 5/77:00 amORF - ORD

1 stop4h 41mAmerican Airlines

Deal found 4/1

$146

qui 6/1211:35 amORF - MDW

2 stops33h 11mAllegiant Air

Deal found 4/1

$147

qui 5/293:11 pmORF - MDW

2 stops29h 03mMultiple Airlines

Deal found 4/2

$158

ter 8/58:25 amORF - ORD

1 stop4h 44mDelta

Deal found 4/1

$163

qua 5/286:40 amORF - ORD

2 stops7h 05mSouthwest

Deal found 4/1

$168

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

ter 4/29

6:00 am-9:24 am

1 stop28h 24m

Chicago O'Hare Intl

ter 5/6

11:47 am-10:29 am

1 stop21h 42m

$233

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

sáb 5/24

12:13 pm-8:03 pm

1 stop8h 50m

Chicago O'Hare Intl

dom 5/25

7:47 am-9:36 am

1 stop24h 49m

$237

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

qui 4/17

10:09 am-5:31 pm

1 stop8h 22m

Chicago Midway

dom 4/20

12:46 pm-4:58 pm

1 stop27h 12m

$240

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

qui 4/17

5:41 pm-8:49 am

1 stop16h 08m

Chicago O'Hare Intl

qui 4/24

4:30 pm-7:32 pm

1 stop26h 02m

$240

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

ter 6/10

5:25 am-6:30 am

Nonstop2h 05m

Chicago Midway

qua 6/11

7:00 pm-10:00 pm

Nonstop2h 00m

$271

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

ter 6/10

5:05 pm-6:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

qua 6/11

11:10 am-2:29 pm

Nonstop2h 19m

$271

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

qua 8/27

5:55 pm-7:35 pm

Nonstop2h 40m

Chicago O'Hare Intl

dom 8/31

2:04 pm-5:25 pm

Nonstop2h 21m

$285

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

qua 5/21

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

sáb 5/24

4:15 pm-11:25 pm

1 stop6h 10m

$288

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

ter 4/22

8:00 am-12:05 pm

1 stop5h 05m

Chicago O'Hare Intl

qua 4/30

5:30 am-12:19 pm

1 stop5h 49m

$291

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

ter 6/10

6:10 am-11:50 am

1 stop6h 40m

Chicago O'Hare Intl

qua 6/11

11:25 am-10:35 pm

2 stops10h 10m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 24 results

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?

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?

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?

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

The most flights from C6E to CHI are scheduled on a Monday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Rainfall in Chicago 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

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 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

4,274 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest

8.0

Very good

4,274 reviews

Southwest

8.0

Very good

4,274 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta

8.0

Very good

7,897 reviews

Southwest

8.0

Very good

4,274 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines

7.4

Good

8,616 reviews

Southwest

8.0

Very good

4,274 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Allegiant Air

7.3

Good

732 reviews

Southwest

8.0

Very good

4,274 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,274 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

What are the cheapest airlines to fly from Chesapeake to Chicago one-way?
$90 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 Allegiant Air, with prices starting from $99 and $105, 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: Qatar Airways (79%), ANA (79%), Royal Jordanian (76%).
What are the cheapest flights from Chesapeake to Chicago?
Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $1,555, our data indicates the cheapest price to be $138. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $192.
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

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Top 5 airlines flying from Chesapeake to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$105	Average$230	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$176	Average$472	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$188	Average$391	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$250	Average$394	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$268	Average$384	FlexibilityNo cancel fee	On-time63%

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$86+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chesapeake to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or April, 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 abril 3, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chesapeake to Chicago

Cheapest flights from Chesapeake to ChicagoExplore 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 abril 3, 2025.

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 abril 3, 2025.

Cheapflights Fare Finder

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

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.

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 March 28, 2025.

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

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 abril 3, 2025.

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.

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 abril 3, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

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.

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?

What are the most popular routes from Chesapeake to Chicago?

What are the most reliable airlines from Chesapeake to Chicago?

What are the cheapest flights from Chesapeake to Chicago?

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

How can I find direct flights from Chesapeake to Chicago?

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

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

Traveling to a place near Chesapeake?

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 5 airlines flying from Chesapeake to Chicago

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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 abril 3, 2025.