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Cheap flights from Charlottesville to Chicago from $229

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Charlottesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:03 pm - 11:47 pmCHO-MDW
6h 44m1 stop
Delta Logo
6:00 am - 2:23 pmMDW-CHO
7h 23m1 stop
$229Delta
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
6:00 am - 9:53 amCHO-MDW
4h 53m1 stop
Delta Logo
10:47 am - 5:26 pmMDW-CHO
5h 39m1 stop
$304Delta
Find Deal
Sat, Nov 15 - Tue, Nov 18
Delta Logo
3:05 pm - 9:45 pmCHO-MDW
7h 40m1 stop
Delta Logo
6:00 am - 11:16 amMDW-CHO
4h 16m1 stop
$314Delta
Find Deal
Tue, Apr 21 - Sat, Apr 25
Delta Logo
3:05 pm - 9:45 pmCHO-MDW
7h 40m1 stop
Delta Logo
6:00 am - 11:16 amMDW-CHO
4h 16m1 stop
$334Delta
Find Deal
Tue, Apr 21 - Sat, Apr 25
Delta Logo
6:00 am - 11:55 amCHO-MDW
6h 55m1 stop
Delta Logo
6:00 am - 11:19 amMDW-CHO
4h 19m1 stop
$349Delta
Find Deal
Thu, Dec 11 - Sun, Dec 14
Delta Logo
6:00 am - 11:52 amCHO-MDW
6h 52m1 stop
Delta Logo
4:28 pm - 10:47 pmMDW-CHO
5h 19m1 stop
$354Delta
Find Deal
Tue, Nov 18 - Sat, Nov 22
Delta Logo
6:00 am - 9:58 amCHO-MDW
4h 58m1 stop
Delta Logo
6:00 am - 11:18 amMDW-CHO
4h 18m1 stop
$384Delta
Find Deal
Thu, Feb 5 - Sun, Feb 8
Delta Logo
5:37 pm - 10:22 pmCHO-MDW
5h 45m1 stop
Delta Logo
6:00 am - 12:47 pmMDW-CHO
5h 47m1 stop
$434Delta
Find Deal
Sat, Dec 20 - Thu, Dec 25
Delta Logo
6:00 am - 11:55 amCHO-MDW
6h 55m1 stop
Delta Logo
6:00 am - 11:19 amMDW-CHO
4h 19m1 stop
$467Delta
Find Deal
Thu, Dec 11 - Fri, Dec 12
Delta Logo
5:30 pm - 10:44 pmCHO-MDW
6h 14m1 stop
Delta Logo
6:00 am - 3:15 pmMDW-CHO
8h 15m1 stop
$483Delta
Find Deal
Wed, Mar 4 - Sat, Mar 7

Delta flights from Charlottesville to Chicago Midway Airport

Our best Delta deals on Charlottesville to Chicago Midway Airport flight tickets
Delta
Dec 5
CHO6:03 pmCharlottesville Albemarle
6h 44m
1 stop
MDW11:47 pmChicago Midway
Dec 7
MDW6:00 amChicago Midway
7h 23m
1 stop
CHO2:23 pmCharlottesville Albemarle
$229
Find similar
Delta
Nov 15
CHO6:00 amCharlottesville Albemarle
4h 53m
1 stop
MDW9:53 amChicago Midway
Nov 18
MDW10:47 amChicago Midway
5h 39m
1 stop
CHO5:26 pmCharlottesville Albemarle
$304
Find similar
Delta
Apr 21
CHO3:05 pmCharlottesville Albemarle
7h 40m
1 stop
MDW9:45 pmChicago Midway
Apr 25
MDW6:00 amChicago Midway
4h 16m
1 stop
CHO11:16 amCharlottesville Albemarle
$314
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Charlottesville to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated November 4, 2025.
Use the filters below to find and compare flights from Charlottesville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 12/5

6:03 pm-11:47 pm

1 stop6h 44m

Chicago Midway

Sun 12/7

6:00 am-2:23 pm

1 stop7h 23m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 11/15

6:00 am-9:53 am

1 stop4h 53m

Chicago Midway

Tue 11/18

10:47 am-5:26 pm

1 stop5h 39m

$304

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 4/21

3:05 pm-9:45 pm

1 stop7h 40m

Chicago Midway

Sat 4/25

6:00 am-11:16 am

1 stop4h 16m

$314

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 4/21

3:05 pm-9:45 pm

1 stop7h 40m

Chicago Midway

Sat 4/25

6:00 am-11:16 am

1 stop4h 16m

$334

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 12/11

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Sun 12/14

6:00 am-11:19 am

1 stop4h 19m

$349

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 11/18

6:00 am-11:52 am

1 stop6h 52m

Chicago Midway

Sat 11/22

4:28 pm-10:47 pm

1 stop5h 19m

$354

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 2/5

6:00 am-9:58 am

1 stop4h 58m

Chicago Midway

Sun 2/8

6:00 am-11:18 am

1 stop4h 18m

$384

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 12/20

5:37 pm-10:22 pm

1 stop5h 45m

Chicago Midway

Thu 12/25

6:00 am-12:47 pm

1 stop5h 47m

$434

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 12/11

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Fri 12/12

6:00 am-11:19 am

1 stop4h 19m

$467

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 3/4

5:30 pm-10:44 pm

1 stop6h 14m

Chicago Midway

Sat 3/7

6:00 am-3:15 pm

1 stop8h 15m

$483

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Charlottesville to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Charlottesville Albemarle to Chicago Midway?

Delta is the most popular carrier operating from Charlottesville Albemarle to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Charlottesville according to our data. Southwest is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

When to book flights from Charlottesville to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Charlottesville to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Charlottesville to Chicago Midway Airport (CHO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Chicago Midway Airport

Direct flights

None
There are no direct flights from Charlottesville to Chicago Midway Airport. There are no popular flight routes from Charlottesville to Chicago Midway Airport.
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  • How far is Charlottesville Albemarle to Chicago Midway by plane?

    Chicago Midway is 554.6 mi away from Charlottesville Albemarle. 4h 52m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Charlottesville Albemarle Airport to Chicago Midway Airport?

    Prices for flights from Charlottesville Albemarle Airport to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Charlottesville Albemarle Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Charlottesville Albemarle Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Charlottesville to Chicago?

It is quick and easy to find Charlottesville to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Charlottesville to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Charlottesville which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Charlottesville to Chicago?

Once you have performed a search for Charlottesville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Charlottesville to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Charlottesville are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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