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Cheap flights from Charlottesville to Chicago from $264

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 7/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Charlottesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:38 pm - 10:36 pm
CHO
-
MDW
5h 58m
1 stop
Delta Logo
6:05 am - 1:52 pm
MDW
-
CHO
6h 47m
1 stop
$289Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
4:30 pm - 10:36 pm
CHO
-
MDW
7h 06m
1 stop
Delta Logo
6:05 am - 11:18 am
MDW
-
CHO
4h 13m
1 stop
$309Delta
Wed, Sep 2 - Wed, Sep 9
Delta Logo
6:00 am - 10:05 am
CHO
-
MDW
5h 05m
1 stop
Delta Logo
6:00 am - 1:52 pm
MDW
-
CHO
6h 52m
1 stop
$329Delta
Wed, Jul 15 - Tue, Jul 21
Delta Logo
6:00 am - 9:59 am
CHO
-
MDW
4h 59m
1 stop
Delta Logo
6:05 am - 11:18 am
MDW
-
CHO
4h 13m
1 stop
$344Delta
Wed, Sep 2 - Wed, Sep 9
Delta Logo
6:00 am - 10:05 am
CHO
-
MDW
5h 05m
1 stop
Delta Logo
6:00 am - 11:27 am
MDW
-
CHO
4h 27m
1 stop
$364Delta
Tue, Jul 14 - Wed, Jul 22
Delta Logo
6:00 am - 10:05 am
CHO
-
MDW
5h 05m
1 stop
Delta Logo
6:05 am - 11:32 am
MDW
-
CHO
4h 27m
1 stop
$394Delta
Wed, Jul 29 - Wed, Aug 5
Delta Logo
6:00 am - 10:05 am
CHO
-
MDW
5h 05m
1 stop
Delta Logo
5:10 pm - 11:14 pm
MDW
-
CHO
5h 04m
1 stop
$399Delta
Tue, Jul 14 - Fri, Jul 24
Delta Logo
4:02 pm - 10:15 pm
CHO
-
MDW
7h 13m
1 stop
Delta Logo
6:00 am - 1:52 pm
MDW
-
CHO
6h 52m
1 stop
$414Delta
Sat, Jul 25 - Thu, Jul 30
Delta Logo
5:38 pm - 10:15 pm
CHO
-
MDW
5h 37m
1 stop
Delta Logo
5:10 pm - 11:14 pm
MDW
-
CHO
5h 04m
1 stop
$424Delta
Thu, Jul 16 - Tue, Jul 21
Delta Logo
6:00 am - 9:59 am
CHO
-
MDW
4h 59m
1 stop
Delta Logo
6:05 am - 1:52 pm
MDW
-
CHO
6h 47m
1 stop
$434Delta
Thu, Aug 20 - Mon, Aug 24

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Delta flights from Charlottesville to Chicago Midway Airport

Our best Delta deals on Charlottesville to Chicago Midway Airport flight tickets
Delta
Aug 21
CHO5:38 pmCharlottesville Albemarle
5h 58m
1 stop
MDW10:36 pmChicago Midway
Aug 25
MDW6:05 amChicago Midway
6h 47m
1 stop
CHO1:52 pmCharlottesville Albemarle
$289
Delta
Sep 2
CHO4:30 pmCharlottesville Albemarle
7h 06m
1 stop
MDW10:36 pmChicago Midway
Sep 9
MDW6:05 amChicago Midway
4h 13m
1 stop
CHO11:18 amCharlottesville Albemarle
$309
Delta
Jul 15
CHO6:00 amCharlottesville Albemarle
5h 05m
1 stop
MDW10:05 amChicago Midway
Jul 21
MDW6:00 amChicago Midway
6h 52m
1 stop
CHO1:52 pmCharlottesville Albemarle
$329

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 July 4, 2026.
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

Cheapest round-trip

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 8/21

5:38 pm-10:36 pm

1 stop5h 58m

Chicago Midway

Mon 8/24

6:05 am-1:52 pm

1 stop6h 47m

$289

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/2

4:30 pm-10:36 pm

1 stop7h 06m

Chicago Midway

Wed 9/9

6:05 am-11:18 am

1 stop4h 13m

$309

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 7/15

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Tue 7/21

6:00 am-1:52 pm

1 stop6h 52m

$329
Quickest round-trip

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/2

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Wed 9/9

6:05 am-11:18 am

1 stop4h 13m

$344

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 7/14

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Wed 7/22

6:00 am-11:27 am

1 stop4h 27m

$364

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 7/29

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Wed 8/5

6:05 am-11:32 am

1 stop4h 27m

$394

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 7/14

6:00 am-10:05 am

1 stop5h 05m

Chicago Midway

Fri 7/24

5:10 pm-11:14 pm

1 stop5h 04m

$399

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 7/25

4:02 pm-10:15 pm

1 stop7h 13m

Chicago Midway

Thu 7/30

6:00 am-1:52 pm

1 stop6h 52m

$414

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 7/16

5:38 pm-10:15 pm

1 stop5h 37m

Chicago Midway

Tue 7/21

5:10 pm-11:14 pm

1 stop5h 04m

$424

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 8/20

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Mon 8/24

6:05 am-1:52 pm

1 stop6h 47m

$434

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 73% 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

Fastest flight time

4h 58m

Direct flights

None
The fastest flight from Charlottesville to Chicago Midway Airport takes 4h 58m
There are no direct flights from Charlottesville to Chicago Midway Airport. There are no popular flight routes from Charlottesville to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Charlottesville to Chicago Midway Airport

  • How far is Charlottesville Albemarle to Chicago Midway by plane?

    Chicago Midway is 554.6 mi away from Charlottesville Albemarle. 4h 58m 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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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