How long is the flight from Chesapeake to Chicago?

Southwest, United Airlines, and Spirit Airlines can get you from Chesapeake to Chicago in just under 2h 15m. Your travel time can differ by up to 9h 46m. There are 702 mi between Chesapeake and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

$72 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $98 and $119, respectively.

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.

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).

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 $840, our data indicates the cheapest price to be $124. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $138.

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 (80%), Avianca (75%), GoJet (74%).

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

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

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.

$45+ Flights from Chesapeake to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Chesapeake to Chicago with Cheapflights

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”

2. Select your favorite providers

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.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or October, booked 78 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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, 2025.

Wed 12/3111:44 amORF - ORD

1 stop11h 40mFrontier

Sat 1/36:10 amORD - ORF

1 stop9h 17mFrontier

Deal found 12/22

$282

Tue 12/303:11 pmORF - MDW

1 stop7h 47mFrontier

Fri 1/26:12 amMDW - ORF

1 stop6h 27mFrontier

Deal found 12/22

$337

Tue 12/303:11 pmORF - ORD

1 stop20h 07mFrontier

Fri 1/26:00 amORD - ORF

1 stop6h 39mFrontier

Deal found 12/22

$337

Wed 12/3111:44 amORF - MDW

1 stop11h 28mFrontier

Mon 1/56:12 amMDW - ORF

1 stop5h 57mFrontier

Deal found 12/22

$342

Wed 12/3111:44 amORF - ORD

1 stop11h 40mFrontier

Mon 1/56:00 amORD - ORF

1 stop6h 09mFrontier

Deal found 12/22

$342

Wed 12/313:18 pmORF - ORD

Nonstop2h 33mAmerican Airlines

Mon 1/511:40 amORD - ORF

Nonstop2h 08mAmerican Airlines

Deal found 12/22

$352

Wed 12/2411:44 amORF - MDW

1 stop11h 28mFrontier

Sat 12/278:15 amMDW - ORF

1 stop7h 12mFrontier

Deal found 12/22

$362

Wed 12/2411:44 amORF - ORD

1 stop7h 49mFrontier

Sat 12/276:10 amORD - ORF

1 stop9h 17mFrontier

Deal found 12/22

$362

Wed 12/3111:44 amORF - ORD

1 stop11h 40mMultiple Airlines

Sun 1/410:49 pmORD - ORF

2 stops38h 17mMultiple Airlines

Deal found 12/22

$367

Fri 12/262:34 pmORF - ORD

1 stop8h 50mFrontier

Sat 12/276:10 amORD - ORF

1 stop9h 17mFrontier

Deal found 12/22

$402

Tue 12/303:11 pmORF - MDW

2 stops32h 01mMultiple Airlines

Mon 1/53:10 pmMDW - ORF

1 stop26h 35mMultiple Airlines

Deal found 12/21

$419

Fri 12/262:34 pmORF - MDW

1 stop8h 38mFrontier

Sat 12/276:12 amMDW - ORF

1 stop9h 15mFrontier

Deal found 12/22

$427

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 December 23, 2025.

Tue 2/245:35 pmORF - MDW

Nonstop2h 15mSouthwest

Sat 2/286:05 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/22

$263

Tue 2/244:55 pmORF - ORD

Nonstop2h 35mUnited Airlines

Sat 2/2811:05 amORD - ORF

Nonstop2h 17mUnited Airlines

Deal found 12/22

$263

Fri 2/136:45 amORF - ORD

1 stop12h 01mSpirit Airlines

Sun 2/1512:44 pmORD - ORF

1 stop8h 06mSpirit Airlines

Deal found 12/22

$286

Fri 1/236:00 amORF - ORD

1 stop6h 35mAmerican Airlines

Tue 1/277:25 pmORD - ORF

Nonstop2h 07mAmerican Airlines

Deal found 12/20

$314

Fri 1/231:01 pmORF - ORD

1 stop4h 37mDelta

Tue 1/278:50 amORD - ORF

1 stop7h 44mDelta

Deal found 12/20

$324

Wed 2/2510:15 amORF - ORD

Nonstop2h 35mUnited Airlines

Sat 2/2811:05 amORD - ORF

Nonstop2h 17mUnited Airlines

Deal found 12/22

$263

Sat 1/1711:15 amORF - MDW

1 stop6h 40mSouthwest

Mon 1/196:10 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/22

$300

Sat 1/1710:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Mon 1/196:10 pmORD - ORF

Nonstop2h 22mUnited Airlines

Deal found 12/22

$290

Wed 3/111:42 pmORF - ORD

1 stop5h 39mAmerican Airlines

Sat 3/143:04 pmORD - ORF

Nonstop2h 08mAmerican Airlines

Deal found 12/21

$332

Wed 3/1112:36 pmORF - MDW

1 stop6h 18mDelta

Sat 3/144:30 pmMDW - ORF

1 stop4h 50mDelta

Deal found 12/21

$342

Thu 4/2310:05 amORF - MDW

1 stop6h 00mSouthwest

Sat 4/257:50 amMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/21

$313

Sun 1/185:35 pmORF - MDW

Nonstop2h 15mSouthwest

Sun 1/256:10 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/21

$315

Sun 1/1810:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Sun 1/254:15 pmORD - ORF

1 stop6h 12mUnited Airlines

Deal found 12/21

$325

Wed 2/114:45 pmORF - ORD

Nonstop2h 35mUnited Airlines

Sun 2/156:02 pmORD - ORF

Nonstop2h 09mUnited Airlines

Deal found 12/21

$329

Mon 4/1310:05 amORF - MDW

1 stop6h 00mSouthwest

Wed 4/226:05 pmMDW - ORF

Nonstop2h 05mSouthwest

Deal found 12/20

$333

Fri 12/2610:05 pmORF - RFD

2 stops34h 46mMultiple Airlines

Tue 12/307:54 pmRFD - ORF

1 stop15h 16mMultiple Airlines

Deal found 12/21

$934

Tue 2/2410:15 amORF - ORD

Nonstop2h 35mUnited Airlines

Sun 3/111:05 amORD - ORF

Nonstop2h 18mUnited Airlines

Deal found 12/22

$329

Last-minute flights from Chesapeake to Chicago
Discover last-minute flight deals from Chesapeake to Chicago. Data last updated December 23, 2025 and is based on user searches.

Tue 12/303:11 pmORF - MDW

1 stop7h 47mFrontier

Fri 1/26:12 amMDW - ORF

1 stop6h 27mFrontier

Deal found 12/22

$337

Wed 12/3111:44 amORF - ORD

1 stop11h 40mFrontier

Sat 1/36:10 amORD - ORF

1 stop9h 17mFrontier

Deal found 12/22

$282

Mon 1/53:01 pmORF - ORD

2 stops42h 30mSpirit Airlines

Fri 1/97:20 amORD - ORF

1 stop10h 18mSpirit Airlines

Deal found 12/21

$270

Mon 1/57:40 pmORF - ORD

1 stop21h 39mMultiple Airlines

Fri 1/95:15 amORD - ORF

1 stop12h 23mMultiple Airlines

Deal found 12/21

$291

Wed 1/73:01 pmORF - ORD

1 stop10h 13mSpirit Airlines

Sat 1/1010:48 amORD - ORF

1 stop10h 02mSpirit Airlines

Deal found 12/21

$255

Wed 1/73:01 pmORF - ORD

3 stops28h 15mSpirit Airlines

Sun 1/115:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/23

$276

Sat 1/1710:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Mon 1/196:10 pmORD - ORF

Nonstop2h 22mUnited Airlines

Deal found 12/22

$290

Sat 1/1711:15 amORF - MDW

1 stop6h 40mSouthwest

Mon 1/196:10 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/22

$300

Sun 1/186:45 amORF - ORD

2 stops16h 57mSpirit Airlines

Sun 1/254:38 pmORD - ORF

2 stops25h 00mSpirit Airlines

Deal found 12/21

$259

Sun 1/185:35 pmORF - MDW

Nonstop2h 15mSouthwest

Sun 1/256:10 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/21

$315

Tue 1/2010:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Tue 1/2711:12 amORD - ORF

Nonstop2h 20mUnited Airlines

Deal found 12/23

$249

Fri 1/237:32 amORF - ORD

Nonstop2h 38mAmerican Airlines

Tue 1/277:25 pmORD - ORF

Nonstop2h 07mAmerican Airlines

Deal found 12/20

$304

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 December 23, 2025.

Wed 2/46:15 pmORF - ORD

1 stop6h 32mSpirit Airlines

Deal found 12/21

$45

Mon 1/127:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/21

$55

Sat 2/1412:29 pmORF - ORD

1 stop8h 18mMultiple Airlines

Deal found 12/22

$63

Wed 2/187:31 pmORF - ORD

1 stop28h 53mMultiple Airlines

Deal found 12/20

$64

Thu 1/157:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/23

$65

Sat 1/176:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Deal found 12/22

$67

Sat 1/316:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Deal found 12/22

$68

Sat 2/79:10 pmORF - MDW

1 stop23h 42mFrontier

Deal found 12/21

$70

Thu 1/226:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Deal found 12/23

$70

Wed 1/712:25 pmORF - ORD

1 stop11h 14mFrontier

Deal found 12/23

$71

Fri 1/237:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/22

$72

Thu 2/196:45 amORF - ORD

1 stop12h 01mSpirit Airlines

Deal found 12/23

$74

Find flight deals from Chesapeake to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$254 (Kiwi.com)
One-way from	$45 (Priceline)
Popular in	December
Cheapest in	September
Average price	$390

Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.

Search Deals

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 ($10 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

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 - MDW

ORFMDW

Norfolk

Tue 2/24

5:35 pm-6:50 pm

Nonstop2h 15m

Chicago Midway

Sat 2/28

6:05 pm-9:05 pm

Nonstop2h 00m

$263

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 2/24

4:55 pm-6:30 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 2/28

11:05 am-2:22 pm

Nonstop2h 17m

$263

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 2/25

10:15 am-11:50 am

Nonstop2h 35m

Chicago O'Hare Intl

Sat 2/28

11:05 am-2:22 pm

Nonstop2h 17m

$263

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 2/13

6:45 am-5:46 pm

1 stop12h 01m

Chicago O'Hare Intl

Sun 2/15

12:44 pm-9:50 pm

1 stop8h 06m

$286

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 1/17

10:05 am-11:40 am

Nonstop2h 35m

Chicago O'Hare Intl

Mon 1/19

6:10 pm-9:32 pm

Nonstop2h 22m

$290

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 1/17

11:15 am-4:55 pm

1 stop6h 40m

Chicago Midway

Mon 1/19

6:10 pm-9:10 pm

Nonstop2h 00m

$300

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 4/23

10:05 am-3:05 pm

1 stop6h 00m

Chicago Midway

Sat 4/25

7:50 am-10:50 am

Nonstop2h 00m

$313

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/23

6:00 am-11:35 am

1 stop6h 35m

Chicago O'Hare Intl

Tue 1/27

7:25 pm-10:32 pm

Nonstop2h 07m

$314

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 1/18

5:35 pm-6:50 pm

Nonstop2h 15m

Chicago Midway

Sun 1/25

6:10 pm-9:10 pm

Nonstop2h 00m

$315

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/23

1:01 pm-4:38 pm

1 stop4h 37m

Chicago O'Hare Intl

Tue 1/27

8:50 am-5:34 pm

1 stop7h 44m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 39 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 78 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, May is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $108). Flying from Chesapeake to Chicago in July is currently the most expensive (average of $265). 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?

A simple way to save on the total cost of your ticket is to fly from Chesapeake to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 17% on your trip compared to booking a flight in the evening.

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 Saturday mornings when fares are most often at their lowest. Sunday evenings 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 Friday (24 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (11 on average).

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Chesapeake to Chicago, such as Southwest, United Airlines, and American 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

4,253 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Southwest

8.0

Very good

4,253 reviews

Southwest

8.0

Very good

4,253 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

United Airlines

7.4

Good

9,105 reviews

Southwest

8.0

Very good

4,253 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

American Airlines

7.2

Good

11,054 reviews

Southwest

8.0

Very good

4,253 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Spirit Airlines

6.3

Okay

8,196 reviews

Southwest

8.0

Very good

4,253 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Frontier

5.8

Fair

3,075 reviews

Southwest

8.0

Very good

4,253 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

How long is the flight from Chesapeake to Chicago?
Southwest, United Airlines, and Spirit Airlines can get you from Chesapeake to Chicago in just under 2h 15m. Your travel time can differ by up to 9h 46m. There are 702 mi between Chesapeake and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.
What are the cheapest airlines to fly from Chesapeake to Chicago one-way?
$72 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $98 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: ANA (80%), Avianca (75%), GoJet (74%).
What are the cheapest flights from Chesapeake to Chicago?
Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $840, our data indicates the cheapest price to be $124. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $138.
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, May is the cheapest month in which you can book a flight from Chesapeake to Chicago (average of $108). Flying from Chesapeake to Chicago in July is currently the most expensive (average of $265). 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

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Top 6 airlines flying from Chesapeake to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$65	Average$249	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$108	Average$367	FlexibilityNo cancel fee	On-timeN/A
Frontier	Cheapest$176	Average$208	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$181	Average$364	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$215	Average$386	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$216	Average$362	FlexibilityNo cancel fee	On-time71%

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$45+ 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 2/4. 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

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3. Compare prices and book

Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or October, booked 78 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 December 23, 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 December 23, 2025.

Find flight deals from Chesapeake to Chicago

Keep the following information in mind while searching for Chesapeake to Chicago flight deals. Data was last updated December 23, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

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 December 19, 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 December 23, 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 December 20, 2025.

Weekly flight availability from Chesapeake to Chicago

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Chesapeake to Chicago, such as Southwest, United Airlines, and American Airlines. You can also see how each airline stacks up 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.

How long is the flight from Chesapeake to Chicago?

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 Chicago?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chesapeake to Chicago

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Top 6 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 December 23, 2025.