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Cheap flights from Chesapeake to Chicago (ORF - CHI)

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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 Tuesday

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

ORF - CHI
Price
$229 - $297
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 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

One-way from

$66

One-way flight from Chesapeake to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chesapeake to Chicago?

Flights from Chesapeake to Chicago are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 20 days in advance, which can save you up to 10% on flights from Chesapeake to Chicago compared to booking the week you need them. Waiting 20 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $137. For sooner than that we have options available in the next 3 days from $157.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Chesapeake in April are about $135 on average during April, but can be found for as low as $33.

When is the cheapest time to fly from Chesapeake to Chicago (ORF - CHI)?

It’s typically best to fly out from Chesapeake to Chicago in the evening. Doing so could potentially save you 6% on the flight price compared to flying at noon, which is usually more expensive.

Cheap flights from Chesapeake to Chicago in January, February 2021

The best prices found for ORF to CHI flights for January, February
1 Feb - 8 Feb
$88pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
6 Feb - 8 Feb
$93pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
1 Feb - 5 Feb
$98pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk

Chesapeake to Chicago 2021 flight deals

Cheap flights to Chicago from Chesapeake found for this year
1 Feb - 8 Feb
$88pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
6 Feb - 8 Feb
$93pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
1 Feb - 5 Feb
$98pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk

Non-stop flights to Chicago from Chesapeake

Save time with Chesapeake to Chicago direct flight deals
24 Feb - 2 Mar
$211pp
ORF
Norfolk
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ORF
Norfolk
22 Feb - 26 Feb
$221pp
ORF
Norfolk
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ORF
Norfolk
11 Feb - 13 Feb
$235pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk

Last minute flights from Chesapeake to Chicago

Late deals on round-trip flights to Chicago from Chesapeake, departing today and this week
29 Jan - 31 Jan
$115pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
25 Jan - 29 Jan
$139pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
ORF
Norfolk
29 Jan - 31 Jan
$165pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
ORF
Norfolk

One-way flights to Chicago from Chesapeake

The cheapest one-way flights from Chesapeake to Chicago
5:20 am - 6:44 pm
Frontier
1 Stop
14h 24m
ORF - ORD
Frontier
$66
Kiwi.com
8:52 am - 12:54 pm
American Airlines
1 Stop
5h 02m
ORF - ORD
American Airlines
3:30 pm - 2:34 am
United Airlines
2 Stops
12h 04m
ORF - ORD
United Airlines
$218
United

Related info for your journey

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

Flight FAQs

From Chesapeake to Chicago

Are flight prices decreasing from Norfolk to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Norfolk and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Norfolk to Chicago to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Norfolk to Chicago. Policies will vary by airline.

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

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, American Airlines, and Delta flying from Norfolk to Chicago have implemented new flexible cancellation policies.

Can I find flights from Chesapeake to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Chesapeake to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $88, but on average you can expect to pay $146.

Are there nonstop flights from Chesapeake to Chicago for under $300 on Cheapflights?

Cheapflights has at least 8 direct flights from Chesapeake to Chicago under $300. A good price for a nonstop flight from Chesapeake to Chicago is less than $277.

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.

Is Norfolk weather warmer or cooler than Chicago?

With an average temperature of 90 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago are colder than in Norfolk.

How long is the flight from Chesapeake to Chicago?

Departing from Chesapeake to Chicago will take you 2h 30m. Both multi-stop and nonstop flights can be found to your destination and back.

What is the cheapest airline to fly from Chesapeake to Chicago round-trip?

According to our current data, Frontier ($88), offers the cheapest pricing from Chesapeake to Chicago. Frontier is 65% cheaper than the average price of flights available within the next 90 days to this destination.

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

The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $66. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chesapeake to Chicago for a low price.

Alternative routes for Chesapeake to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Chesapeake to Chicago
Flight duration
2h 23m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Norfolk

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 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.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$87 $218 No cancel fee 62%
American Airlines
$109 $266 No cancel fee 71%
United Airlines
$113 $322 No cancel fee 69%
Delta
$113 $354 No cancel fee N/A

Hourly flight availability from Chesapeake to Chicago

Early morning Midnight to 6 AM 50% of ORF to CHI departures
Morning 6 AM to noon 25% of ORF to CHI departures
Afternoon Noon to 6 PM 16% of ORF to CHI departures
Evening 6 PM to midnight 9% of ORF to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chesapeake to Chicago
Sunday
10 daily flights
Monday
10 daily flights
Tuesday
8 daily flights
Wednesday
8 daily flights
Thursday
12 daily flights
Friday
12 daily flights
Saturday
14 daily flights
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