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Cheap flights from Charlottesville to Chicago from $110

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 11/12. 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

Delta Logo
5:35 am - 9:40 amCHO-MDW
5h 05m1 stop
Delta Logo
5:04 pm - 10:49 pmMDW-CHO
4h 45m1 stop
$219Delta
Find Deal
Thu, Oct 16 - Tue, Oct 21
Delta Logo
4:05 pm - 10:14 pmCHO-MDW
7h 09m1 stop
Delta Logo
6:00 am - 11:11 amMDW-CHO
4h 11m1 stop
$229Delta
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
5:42 pm - 9:36 pmCHO-MDW
4h 54m1 stop
Delta Logo
4:25 pm - 11:35 pmMDW-CHO
6h 10m1 stop
$249Delta
Find Deal
Wed, Oct 1 - Sat, Oct 4
Delta Logo
5:35 am - 9:40 amCHO-MDW
5h 05m1 stop
Delta Logo
6:00 am - 1:50 pmMDW-CHO
6h 50m1 stop
$293Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
4:08 pm - 9:10 pmCHO-MDW
6h 02m1 stop
Delta Logo
4:23 pm - 10:49 pmMDW-CHO
5h 26m1 stop
$299Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
4:08 pm - 9:10 pmCHO-MDW
6h 02m1 stop
Delta Logo
4:23 pm - 10:49 pmMDW-CHO
5h 26m1 stop
$303Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
5:35 am - 9:40 amCHO-MDW
5h 05m1 stop
Delta Logo
10:35 am - 5:16 pmMDW-CHO
5h 41m1 stop
$304Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
4:08 pm - 9:10 pmCHO-MDW
6h 02m1 stop
Delta Logo
4:23 pm - 10:49 pmMDW-CHO
5h 26m1 stop
$309Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
6:01 pm - 10:14 pmCHO-MDW
5h 13m1 stop
Delta Logo
5:04 pm - 10:49 pmMDW-CHO
4h 45m1 stop
$323Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
5:35 am - 9:40 amCHO-MDW
5h 05m1 stop
Delta Logo
5:04 pm - 10:49 pmMDW-CHO
4h 45m1 stop
$329Delta
Find Deal
Thu, Oct 16 - Tue, Oct 21

Delta flights from Charlottesville to Chicago Midway Airport

Our best Delta deals on Charlottesville to Chicago Midway Airport flight tickets
Delta
Oct 16
CHO5:35 amCharlottesville Albemarle
5h 05m
1 stop
MDW9:40 amChicago Midway
Oct 21
MDW5:04 pmChicago Midway
4h 45m
1 stop
CHO10:49 pmCharlottesville Albemarle
$219
Find similar
Delta
Oct 25
CHO4:05 pmCharlottesville Albemarle
7h 09m
1 stop
MDW10:14 pmChicago Midway
Oct 28
MDW6:00 amChicago Midway
4h 11m
1 stop
CHO11:11 amCharlottesville Albemarle
$229
Find similar
Delta
Oct 1
CHO5:42 pmCharlottesville Albemarle
4h 54m
1 stop
MDW9:36 pmChicago Midway
Oct 4
MDW4:25 pmChicago Midway
6h 10m
1 stop
CHO11:35 pmCharlottesville Albemarle
$249
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 September 19, 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

Thu 10/16

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Tue 10/21

5:04 pm-10:49 pm

1 stop4h 45m

$219

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 10/25

4:05 pm-10:14 pm

1 stop7h 09m

Chicago Midway

Tue 10/28

6:00 am-11:11 am

1 stop4h 11m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 10/1

5:42 pm-9:36 pm

1 stop4h 54m

Chicago Midway

Sat 10/4

4:25 pm-11:35 pm

1 stop6h 10m

$249

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/23

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Mon 10/27

6:00 am-1:50 pm

1 stop6h 50m

$293

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 10/4

4:08 pm-9:10 pm

1 stop6h 02m

Chicago Midway

Sat 10/11

4:23 pm-10:49 pm

1 stop5h 26m

$299

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 10/4

4:08 pm-9:10 pm

1 stop6h 02m

Chicago Midway

Sat 10/11

4:23 pm-10:49 pm

1 stop5h 26m

$303

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/23

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Mon 10/27

10:35 am-5:16 pm

1 stop5h 41m

$304

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 10/4

4:08 pm-9:10 pm

1 stop6h 02m

Chicago Midway

Sat 10/11

4:23 pm-10:49 pm

1 stop5h 26m

$309

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 10/22

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Mon 10/27

5:04 pm-10:49 pm

1 stop4h 45m

$323

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/16

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Tue 10/21

5:04 pm-10:49 pm

1 stop4h 45m

$329

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 65% 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
Lansing
Portage
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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