Chicago

Cheap flights from Chesapeake to Chicago (C6E - CHI)

The best prices from Chesapeake to Chicago are usually found in May or August, booked 30 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

How to find the cheapest flight from Chesapeake to Chicago

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

$229 - $297

CHI

Temperature

23 - 73.4 °F

CHI

Precipitation

1.7 - 4.9 inches

Popular in

December

High demand for flights, 14% potential price rise

Cheapest in

May

Best time to find cheap flights, 11% potential price drop

Round-trip from

$229

From Chesapeake to Chicago (CHI)

One-way from

$113

One-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 30 days early can save you up to 72% on average compared to booking a flight this week. If booking 30 days before your flight isn’t an option for you, users have found flights from Chesapeake to Chicago for as little as $322 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 $469 for flights departing within the next 3 days.

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

May can be a great time to fly to Chicago from Chesapeake with a flight ticket averaging about $256. Cheapflights users have found deals in the month of May for as cheap as $119. The most expensive prices can be found in the month of December.

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 January, February 2022

The best prices found for Chesapeake to CHI flights for January, February
Feb 3 - Feb 6
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 19m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

12h 25m
$150

Frontier

View Deal

Deal found 1/20/22

Jan 27 - Feb 3
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 21m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

8h 05m
$152

Multiple Airlines

View Deal

Deal found 1/20/22

Feb 10 - Feb 13
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 19m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

12h 25m
$158

Frontier

View Deal

Deal found 1/17/22

Chesapeake to Chicago 2022 flight deals

Cheap flights to Chicago from Chesapeake found for this year
Feb 3 - Feb 6
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 19m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

12h 25m
$150

Frontier

View Deal

Deal found 1/20/22

Jan 27 - Feb 3
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 21m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

8h 05m
$152

Multiple Airlines

View Deal

Deal found 1/20/22

Feb 10 - Feb 13
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 19m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

12h 25m
$158

Frontier

View Deal

Deal found 1/17/22

Non-stop flights to Chicago from Chesapeake

Save time with Chesapeake to Chicago direct flight deals
Feb 19 - Feb 21
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 23m
ORD

Chicago O'Hare Intl

ORF

Norfolk

Nonstop

2h 08m
$197

United Airlines

View Deal

Deal found 1/19/22

Apr 12 - Apr 16
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 21m
ORD

Chicago O'Hare Intl

ORF

Norfolk

Nonstop

2h 14m
$198

Multiple Airlines

View Deal

Deal found 1/18/22

Apr 12 - Apr 15
ORF

Norfolk

ORD

Chicago O'Hare Intl

Nonstop

2h 27m
ORD

Chicago O'Hare Intl

ORF

Norfolk

Nonstop

2h 14m
$208

United Airlines

View Deal

Deal found 1/18/22

Last minute flights from Chesapeake to Chicago

Late deals on return flights to Chicago from Chesapeake, departing today and this week
Jan 27 - Feb 3
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 21m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

8h 05m
$152

Multiple Airlines

View Deal

Deal found 1/20/22

Jan 27 - Feb 3
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 21m
ORD

Chicago O'Hare Intl

ORF

Norfolk

2 stops

10h 34m
$176

Multiple Airlines

View Deal

Deal found 1/20/22

Jan 28 - Jan 30
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

16h 23m
ORD

Chicago O'Hare Intl

ORF

Norfolk

1 stop

12h 25m
$215

Multiple Airlines

View Deal

Deal found 1/17/22

One-way flights to Chicago All airports from Chesapeake

The cheapest one-way flights from Chesapeake to Chicago
Mar 16
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

13h 15m
$63

Frontier

View Deal

Deal found 1/19/22

Mar 22
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

8h 15m
$67

Frontier

View Deal

Deal found 1/17/22

Jan 27
ORF

Norfolk

ORD

Chicago O'Hare Intl

1 stop

28h 21m
$72

Frontier

View Deal

Deal found 1/19/22

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 $150, but on average you can expect to pay $186.

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

Cheapflights has at least 16 direct flights from Chesapeake to Chicago under $200. A good price for a nonstop flight from Chesapeake to Chicago is less than $288.

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: Saturday.

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

On average 2 flights depart from Chesapeake to Chicago per day.
Morning (6am - Noon) - 100% 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 23m. Your travel time can differ by up to 25h 56m. 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?

$63 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 American Airlines, with prices starting from $99 and $107, 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 Major Airline, American Airlines and JetBlue. 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: SkyWest Airlines (91%), Japan Airlines (86%), Royal Jordanian (85%).

What are the cheapest flights from Chesapeake to Chicago?

Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $309, our data indicates the cheapest price to be $39. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $164.

Other flights to Chicago

Can I fly to Chicago from Chesapeake right now?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Chesapeake need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Chesapeake must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Chesapeake are not required to quarantine after entering Chicago.

Can I fly back to Chesapeake from Chicago?

Returning to Chesapeake from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chesapeake.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Chesapeake.

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
Frontier
Cheapest$87
Average$218
FlexibilityNo cancel fee
On-time62%
COVID-19 safety
JetBlue
Cheapest$91
Average$190
FlexibilityNo cancel fee
On-time62%
COVID-19 safety
American Airlines
Cheapest$109
Average$287
FlexibilityNo cancel fee
On-time71%
COVID-19 safety
Delta
Cheapest$113
Average$376
FlexibilityNo cancel fee
On-timeN/A
COVID-19 safety
United Airlines
Cheapest$113
Average$311
FlexibilityNo cancel fee
On-time69%
COVID-19 safety
Spirit Airlines
Cheapest$127
Average$258
FlexibilityNo cancel fee
On-time65%
COVID-19 safety

Hourly flight availability from Chesapeake to Chicago

See what time of day planes typically take off from Chesapeake to Chicago
14%of flight departuresEarly morningMidnight to 6 am
17%of flight departuresMorning6 am to noon
69%of flight departuresAfternoonNoon to 6 pm
0%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
Sunday4daily flights
Monday9daily flights
Tuesday9daily flights
Wednesday9daily flights
Thursday9daily flights
Friday9daily flights
Saturday3daily flights