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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 6/1. 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
5:36 pm - 10:17 pm
CHO
-
MDW
5h 41m
1 stop
Delta Logo
6:00 am - 11:27 am
MDW
-
CHO
4h 27m
1 stop
$289Delta
Wed, Jun 24 - Mon, Jun 29
Delta Logo
5:36 pm - 10:17 pm
CHO
-
MDW
5h 41m
1 stop
Delta Logo
4:25 pm - 11:13 pm
MDW
-
CHO
5h 48m
1 stop
$291Delta
Thu, Jun 25 - Sun, Jun 28
Delta Logo
5:37 pm - 10:15 pm
CHO
-
MDW
5h 38m
1 stop
Delta Logo
6:00 am - 1:52 pm
MDW
-
CHO
6h 52m
1 stop
$299Delta
Thu, Jul 23 - Tue, Jul 28
Delta Logo
5:30 pm - 9:46 pm
CHO
-
MDW
5h 16m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
CHO
7h 29m
1 stop
$309Delta
Wed, Sep 2 - Thu, Sep 10
Delta Logo
6:00 am - 9:59 am
CHO
-
MDW
4h 59m
1 stop
Delta Logo
6:05 am - 11:32 am
MDW
-
CHO
4h 27m
1 stop
$344Delta
Thu, Aug 13 - Sun, Aug 16
Delta Logo
5:38 pm - 10:36 pm
CHO
-
MDW
5h 58m
1 stop
Delta Logo
6:05 am - 11:32 am
MDW
-
CHO
4h 27m
1 stop
$349Delta
Wed, Aug 5 - Sat, Aug 8
Delta Logo
5:39 pm - 9:09 pm
CHO
-
MDW
4h 30m
1 stop
Delta Logo
9:23 am - 11:44 pm
MDW
-
CHO
13h 21m
2 stops
$382Delta
Tue, Jun 2 - Sat, Jun 6
Delta Logo
5:39 pm - 9:09 pm
CHO
-
MDW
4h 30m
1 stop
Delta Logo
6:00 am - 11:27 am
MDW
-
CHO
4h 27m
1 stop
$394Delta
Mon, Jun 1 - Mon, Jun 8
Delta Logo
5:30 pm - 9:46 pm
CHO
-
MDW
5h 16m
1 stop
Delta Logo
6:00 am - 11:16 am
MDW
-
CHO
4h 16m
1 stop
$399Delta
Wed, Sep 2 - Thu, Sep 10
Delta Logo
5:37 pm - 10:15 pm
CHO
-
MDW
5h 38m
1 stop
Delta Logo
6:00 am - 11:27 am
MDW
-
CHO
4h 27m
1 stop
$404Delta
Thu, Jul 23 - Sun, Jul 26

Delta flights from Charlottesville to Chicago Midway Airport

Our best Delta deals on Charlottesville to Chicago Midway Airport flight tickets
Delta
Jun 24
CHO5:36 pmCharlottesville Albemarle
5h 41m
1 stop
MDW10:17 pmChicago Midway
Jun 29
MDW6:00 amChicago Midway
4h 27m
1 stop
CHO11:27 amCharlottesville Albemarle
$289
Delta
Jun 25
CHO5:36 pmCharlottesville Albemarle
5h 41m
1 stop
MDW10:17 pmChicago Midway
Jun 28
MDW4:25 pmChicago Midway
5h 48m
1 stop
CHO11:13 pmCharlottesville Albemarle
$291
Delta
Jul 23
CHO5:37 pmCharlottesville Albemarle
5h 38m
1 stop
MDW10:15 pmChicago Midway
Jul 28
MDW6:00 amChicago Midway
6h 52m
1 stop
CHO1:52 pmCharlottesville Albemarle
$299

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 May 13, 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

Wed 6/24

5:36 pm-10:17 pm

1 stop5h 41m

Chicago Midway

Mon 6/29

6:00 am-11:27 am

1 stop4h 27m

$289

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 6/25

5:36 pm-10:17 pm

1 stop5h 41m

Chicago Midway

Sun 6/28

4:25 pm-11:13 pm

1 stop5h 48m

$291

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 7/23

5:37 pm-10:15 pm

1 stop5h 38m

Chicago Midway

Tue 7/28

6:00 am-1:52 pm

1 stop6h 52m

$299

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/2

5:30 pm-9:46 pm

1 stop5h 16m

Chicago Midway

Thu 9/10

6:00 am-2:29 pm

1 stop7h 29m

$309

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 8/13

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Sun 8/16

6:05 am-11:32 am

1 stop4h 27m

$344

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 8/5

5:38 pm-10:36 pm

1 stop5h 58m

Chicago Midway

Sat 8/8

6:05 am-11:32 am

1 stop4h 27m

$349

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 6/2

5:39 pm-9:09 pm

1 stop4h 30m

Chicago Midway

Sat 6/6

9:23 am-11:44 pm

2 stops13h 21m

$382
Quickest round-trip

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 6/1

5:39 pm-9:09 pm

1 stop4h 30m

Chicago Midway

Mon 6/8

6:00 am-11:27 am

1 stop4h 27m

$394

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/2

5:30 pm-9:46 pm

1 stop5h 16m

Chicago Midway

Thu 9/10

6:00 am-11:16 am

1 stop4h 16m

$399

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 7/23

5:37 pm-10:15 pm

1 stop5h 38m

Chicago Midway

Sun 7/26

6:00 am-11:27 am

1 stop4h 27m

$404

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 71% 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 30m

Direct flights

None
The fastest flight from Charlottesville to Chicago Midway Airport takes 4h 30m
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 30m 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

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