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$55+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Chicago are usually found in September or October, booked 10 days in advance, depart on a Thursday or Friday and return on a Wednesday

Find 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 octubre 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/218:02 pmORF - ORD
1 stop28h 27mMultiple Airlines
dom. 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
Deal found 10/29$189
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/132:00 pmORF - ORD
1 stop10h 06mMultiple Airlines
sáb. 11/1510:52 amORD - ORF
2 stops22h 57mMultiple Airlines
Deal found 10/29$192
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/128:38 amORF - ORD
1 stop6h 43mSpirit Airlines
dom. 12/147:10 amORD - ORF
1 stop11h 06mSpirit Airlines
Deal found 10/30$193
This Priceline deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/1411:43 amORF - ORD
1 stop6h 13mMultiple Airlines
lun. 11/1710:52 amORD - ORF
1 stop7h 06mMultiple Airlines
Deal found 10/28$196
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/126:33 pmORF - ORD
1 stop18h 53mMultiple Airlines
lun. 11/1710:43 pmORD - ORF
2 stops41h 55mMultiple Airlines
Deal found 10/29$197
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/132:00 pmORF - ORD
1 stop10h 06mMultiple Airlines
lun. 11/1711:24 amORD - ORF
2 stops30h 34mMultiple Airlines
Deal found 10/30$199
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/155:40 pmORF - MDW
1 stop5h 32mMultiple Airlines
mié. 12/246:12 amMDW - ORF
2 stops30h 54mMultiple Airlines
Deal found 10/30$200
This Trip.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/156:02 pmORF - ORD
1 stop7h 25mMultiple Airlines
dom. 11/165:01 amORD - ORF
1 stop4h 48mMultiple Airlines
Deal found 10/29$200
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/107:00 amORF - ORD
2 stops18h 09mMultiple Airlines
jue. 12/1112:09 pmORD - ORF
1 stop18h 34mMultiple Airlines
Deal found 10/29$202
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/1212:00 pmORF - MDW
1 stop11h 12mMultiple Airlines
mié. 12/246:12 amMDW - ORF
2 stops30h 54mMultiple Airlines
Deal found 10/30$204
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/132:00 pmORF - ORD
1 stop10h 06mMultiple Airlines
vie. 11/143:26 pmORD - ORF
1 stop24h 31mMultiple Airlines
Deal found 10/29$204
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/133:20 pmORF - ORD
2 stops10h 07mMultiple Airlines
dom. 11/165:25 amORD - ORF
1 stop13h 43mMultiple Airlines
Deal found 10/29$205

Cheap flight deals from Chesapeake to Chicago

Keep the following information in mind while searching for Chesapeake to Chicago flight deals. Data was last updated octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$55
(Priceline)

Popular in

December

Cheapest in

September

Average price

$313
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. 6% potential increase in price ($23 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 October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 30, 2025.
Use the filters below to find and compare flights from Chesapeake to Chicago that are best for you.

Fly from

Chesapeake

Fly to

Chicago

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 11/12

6:33 pm-12:26 pm

1 stop18h 53m

Chicago O'Hare Intl

lun. 11/17

10:43 pm-5:38 pm

2 stops41h 55m

$197

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

sáb. 11/15

6:02 pm-12:27 am

1 stop7h 25m

Chicago O'Hare Intl

dom. 11/16

5:01 am-10:49 am

1 stop4h 48m

$200

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

vie. 12/5

8:38 am-2:21 pm

1 stop6h 43m

Chicago O'Hare Intl

dom. 12/7

5:00 am-7:16 pm

1 stop13h 16m

$205

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

jue. 11/13

2:00 pm-11:06 pm

1 stop10h 06m

Chicago O'Hare Intl

vie. 11/14

7:34 pm-10:49 am

2 stops38h 15m

$206

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

lun. 12/15

5:40 pm-8:46 am

1 stop16h 06m

Chicago Midway

jue. 12/18

6:33 pm-1:39 pm

1 stop18h 06m

$208

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

jue. 12/11

8:38 am-2:21 pm

1 stop6h 43m

Chicago O'Hare Intl

jue. 12/18

7:20 am-6:45 pm

1 stop10h 25m

$219

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

mié. 11/12

6:33 pm-9:12 am

1 stop15h 39m

Chicago Midway

lun. 11/17

9:27 am-10:02 pm

1 stop11h 35m

$234

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 12/3

8:02 pm-11:08 am

1 stop16h 06m

Chicago O'Hare Intl

mié. 12/10

7:10 am-7:43 am

3 stops23h 33m

$240

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

lun. 11/17

11:29 am-4:56 pm

1 stop6h 27m

Chicago O'Hare Intl

vie. 11/21

6:00 am-3:21 pm

1 stop8h 21m

$260

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

mar. 11/25

3:50 pm-10:03 pm

1 stop7h 13m

Chicago Midway

dom. 11/30

5:30 pm-9:43 am

1 stop15h 13m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 53 results
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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?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Chicago. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake to Chicago, you should look to book at least 10 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 December is currently the most expensive (average of $292). 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?

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 octubre 30, 2025.

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 7% on your trip compared to booking a flight in the evening.

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 October 26, 2025.

Travelers seeking maximum savings on their Chesapeake to Chicago flight should consider departing on Monday evenings 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.

How much does it cost to fly round-trip from Chesapeake to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated octubre 30, 2025.
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
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    Spirit Airlines and Frontier can get you from Chesapeake to Chicago in just under 6h 43m. Your travel time can differ by up to 9h 23m. There are 715 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?

    $77 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on United Airlines and Southwest, with prices starting from $129 and $138, 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: Emirates (100%), GoJet (94%), ANA (93%).

  • What are the cheapest flights from Chesapeake to Chicago?

    Looking for the cheapest flight from Chesapeake to Chicago? While on average our users pay $963, our data indicates the cheapest price to be $128. The most popular route (Norfolk - Chicago O'Hare Intl), is priced around $127.

  • 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 December is currently the most expensive (average of $292). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Chesapeake to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chesapeake to Chicago

Discover the top 5 airlines that operate flights from Chesapeake to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$283FlexibilityNo cancel feeOn-time65%
FrontierCheapest$168Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$392FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$229Average$381FlexibilityNo cancel feeOn-time63%

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