Cheap flights from Chesapeake, VA to Chicago (CHI)

RIC — CHI
Oct 4 — Oct 111

The best prices from Chesapeake to Chicago are usually found in February or January, booked 25 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from Chesapeake to Chicago (CHI)

All the information you need to plan the best C6E to CHI flight in 2022: compare Chesapeake to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

C6E - CHI

Price

$218 - $375

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inJuneHigh demand for flights, 21% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 26% potential price drop
Round-trip from$218From Chesapeake to Chicago (CHI)
One-way from$129One-way flight from Chesapeake to Chicago (CHI)

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 24 days early can save you up to 32% on average compared to booking a flight this week. If booking 24 days before your flight isn’t an option for you, users have found flights from Chesapeake to Chicago for as little as $325 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 $398 for flights departing within the next 3 days.

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

February can be a great time to fly to Chicago from Chesapeake with a flight ticket averaging about $296. Cheapflights users have found deals in the month of February for as cheap as $197. The most expensive prices can be found in the month of June.

When is the cheapest time to fly from Chesapeake to Chicago (C6E - 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.

Cheap flights from Chesapeake to Chicago in September, October 2022

The best prices found for Chesapeake to CHI flights for September, October
Oct 4 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

6h 54m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$159

Frontier

Pick Dates

Deal found 9/27/22

Oct 3 - Oct 5
ORF

Norfolk

MDW

Chicago Midway

1 stop

20h 11m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 42m
$164

Frontier

Pick Dates

Deal found 9/27/22

Oct 5 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

16h 40m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$165

Frontier

Pick Dates

Deal found 9/27/22

Chesapeake to Chicago 2022 flight deals

Cheap flights to Chicago from Chesapeake found for this year
Oct 4 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

6h 54m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$159

Frontier

Pick Dates

Deal found 9/27/22

Oct 3 - Oct 5
ORF

Norfolk

MDW

Chicago Midway

1 stop

20h 11m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 42m
$164

Frontier

Pick Dates

Deal found 9/27/22

Oct 5 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

16h 40m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$165

Frontier

Pick Dates

Deal found 9/27/22

Cheap Frontier flights from Chesapeake to Chicago

Oct 4 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

6h 54m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$159

Frontier

Pick Dates

Deal found 9/27/22

Nov 4 - Nov 6
ORF

Norfolk

MDW

Chicago Midway

1 stop

9h 00m
MDW

Chicago Midway

ORF

Norfolk

1 stop

15h 54m
$164

Frontier

Pick Dates

Deal found 9/26/22

Oct 5 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

16h 40m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$165

Frontier

Pick Dates

Deal found 9/27/22

Cheap American Airlines flights from Chesapeake to Chicago

Oct 11 - Oct 11
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

7h 15m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

4h 35m
$190

American Airlines

Pick Dates

Deal found 9/27/22

Dec 6 - Dec 9
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

4h 44m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

6h 49m
$194

American Airlines

Pick Dates

Deal found 9/26/22

Oct 21 - Oct 24
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

6h 21m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

6h 12m
$196

American Airlines

Pick Dates

Deal found 9/27/22

Non-stop flights to Chicago from Chesapeake

Save time with Chesapeake to Chicago direct flight deals
Oct 20 - Oct 24
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 18m
ORD

Chicago O'Hare Intl

ORF

Norfolk

Nonstop

2h 14m
$178

United Airlines

Pick Dates

Deal found 9/27/22

Oct 11 - Oct 11
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 18m
ORD

Chicago O'Hare Intl

ORF

Norfolk

Nonstop

2h 14m
$192

United Airlines

Pick Dates

Deal found 9/27/22

Nov 12 - Nov 14
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 22m
ORD

Chicago O'Hare Intl

ORF

Norfolk

Nonstop

2h 03m
$194

United Airlines

Pick Dates

Deal found 9/28/22

Last minute flights from Chesapeake to Chicago

Late deals on return flights to Chicago from Chesapeake, departing today and this week
Oct 4 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

6h 54m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$159

Frontier

Pick Dates

Deal found 9/27/22

Oct 5 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

16h 40m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$165

Frontier

Pick Dates

Deal found 9/27/22

Oct 8 - Oct 12
ORF

Norfolk

MDW

Chicago Midway

1 stop

14h 29m
MDW

Chicago Midway

ORF

Norfolk

1 stop

5h 44m
$168

Frontier

Pick Dates

Deal found 9/27/22

One-way flights to Chicago from Chesapeake

The cheapest one-way flights from Chesapeake to Chicago
Oct 4
ORF

Norfolk

MDW

Chicago Midway

1 stop

6h 54m
$80

Frontier

Pick Dates

Deal found 9/26/22

Oct 5
ORF

Norfolk

MDW

Chicago Midway

1 stop

16h 40m
$86

Frontier

Pick Dates

Deal found 9/26/22

Oct 26
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 18m
$89

United Airlines

Pick Dates

Deal found 9/26/22

Related info for your journey

Useful info, stats and facts about Chesapeake to Chicago flights.

Which airlines flying from Chesapeake to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chesapeake to Chicago have new flexible policies in place due to COVID-19. United Airlines, American Airlines, and Delta are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from Chesapeake to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Chesapeake to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $164, but on average you can expect to pay $190.

Are there nonstop flights from Chesapeake to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chesapeake to Chicago under $200. A good price for a nonstop flight from Chesapeake to Chicago is less than $246.

Are there last-minute flights available from Chesapeake to Chicago for under $200?

There are currently 20+ open flights from Chesapeake to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Chesapeake to Chicago?

Days when nonstop flights are available for this flight are: Monday, Tuesday, Thursday, Friday, Saturday.

How many flights depart from Chesapeake to Chicago on average per day?

On average 11 flights depart from Chesapeake to Chicago per day.
Early Morning (Midnight to 6am) - 36% of flight departures
Morning (6am - Noon) - 55% of flight departures
Afternoon (Noon - 6pm) - 9% of flight departures

How long is the flight from Chesapeake to Chicago?

Frontier, United Airlines, and American Airlines can get you from Chesapeake to Chicago in just under 2h 18m. Your travel time can differ by up to 6h 42m. There are 644 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?

$80 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $89 and $98, 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 popular airlines that fly from Chesapeake to Chicago?

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

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: Iberia (100%), Republic Airways (91%), ANA (87%).

What are the cheapest flights from Chesapeake to Chicago?

Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $486, our data indicates the cheapest price to be $118. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $187.

Other flights to Chicago

Alternative routes for Chesapeake to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chesapeake to Chicago

The chart below displays the airlines Cheapflights users traveling from Chesapeake to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$16Average$24FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$47Average$158FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
JetBlueCheapest$91Average$190FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
American AirlinesCheapest$98Average$389FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
DeltaCheapest$100Average$356FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$141Average$312FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Chesapeake to Chicago

See what time of day planes typically take off from Chesapeake to Chicago
24%of flight departuresEarly morningMidnight to 6 am
53%of flight departuresMorning6 am to noon
22%of flight departuresAfternoonNoon to 6 pm
1%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chesapeake to Chicago

See how many times per day planes take to the skies headed from Chesapeake to Chicago
Sunday5daily flights
Monday7daily flights
Tuesday8daily flights
Wednesday11daily flights
Thursday17daily flights
Friday6daily flights
Saturday1daily flight