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 Thursday

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

All the information you need to plan the best ORF to CHI flight in 2021: compare Chesapeake to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
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

$158

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 11% on the flight price compared to flying at noon, which is usually more expensive.

Cheap flights from Chesapeake to Chicago in May, June 2021

The best prices found for ORF to CHI flights for May, June
8 Jun - 9 Jun
$228pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ORF
Norfolk
8 Jun - 11 Jun
$255pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
23 Jun - 30 Jun
$255pp
ORF
Norfolk
Allegiant Air
 
1 STOP
RFD
Chicago Greater Rockford
RFD
Chicago Greater Rockford
Allegiant Air
 
1 STOP
ORF
Norfolk

Chesapeake to Chicago 2021 flight deals

Cheap flights to Chicago from Chesapeake found for this year
15 Sep - 20 Sep
$177pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
15 Sep - 20 Sep
$185pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
16 Sep - 20 Sep
$186pp
ORF
Norfolk
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk

Non-stop flights to Chicago from Chesapeake

Save time with Chesapeake to Chicago direct flight deals
15 Sep - 20 Sep
$177pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
22 Aug - 23 Aug
$197pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
2 Sep - 6 Sep
$216pp
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
24 May - 31 May
$274pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
ORF
Norfolk
24 May - 31 May
$281pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
ORF
Norfolk
25 May - 29 May
$290pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
ORF
Norfolk

One-way flights to Chicago from Chesapeake

The cheapest one-way flights from Chesapeake to Chicago
7:09 am - 11:44 am
Delta
1 Stop
5h 35m
ORF - ORD
Delta
$158
DreamWorldTravel
2:45 am - 4:03 am
United Airlines
Nonstop
2h 18m
ORF - ORD
United Airlines
$165
United
5:35 pm - 7:59 pm
Multiple Airlines
1 Stop
27h 24m
ORF - ORD
Multiple Airlines
$169
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chesapeake</span> to <span class="emphasized">Chicago</span> 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.

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.

What airport do you fly from for flights from Norfolk to Chicago?

For a flight from Norfolk to Chicago, you will be flying from Norfolk. Norfolk (ORF) is just 5.9 mi from the center of the city. Norfolk is the only Norfolk airport and it handles 15 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Norfolk on a regular basis.

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 United Airlines for just $177, but on average you can expect to pay $208.

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 $303.

Are there last-minute flights available from Chesapeake to Chicago for under $300?

There are currently 20+ open flights from Chesapeake to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Norfolk to Chicago?

You can find nonstop flights on the following days: Friday.

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 09m. Generally, flights for this route are nonstop.

What are the cheapest airlines flying from Chesapeake to Chicago round-trip?

According to our current data, United Airlines ($177), American Airlines ($193), and Delta ($195) offers the cheapest pricing from Chesapeake to Chicago. United Airlines is 30% 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 United Airlines, with whom users have recently found tickets for as low as $89. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Chesapeake to Chicago for a low price.

Alternative routes for Chesapeake to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Chesapeake to Chicago.
Flight duration
2h 05m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

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

See what time of day planes typically take off from Chesapeake towards Chicago.
Early morning Midnight to 6 AM 36% of ORF to CHI departures
Afternoon Noon to 6 PM 36% of ORF to CHI departures
Morning 6 AM to noon 25% of ORF to CHI departures
Evening 6 PM to midnight 3% of ORF to CHI departures
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.
Sunday
18 daily flights
Monday
16 daily flights
Tuesday
15 daily flights
Wednesday
12 daily flights
Thursday
15 daily flights
Friday
17 daily flights
Saturday
18 daily flights
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