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Cheap flights from Charlottesville to Chicago from $179

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 9/4. 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
5:30 pm - 9:44 pmCHO-MDW
5h 14m1 stop
Delta Logo
10:35 am - 4:47 pmMDW-CHO
5h 12m1 stop
$229Delta
Find Deal
Tue, Nov 11 - Tue, Dec 2
Delta Logo
5:30 pm - 9:44 pmCHO-MDW
5h 14m1 stop
Delta Logo
10:35 am - 4:47 pmMDW-CHO
5h 12m1 stop
$268Delta
Find Deal
Mon, Nov 10 - Wed, Dec 3
Delta Logo
6:01 pm - 10:14 pmCHO-MDW
5h 13m1 stop
Delta Logo
10:35 am - 5:16 pmMDW-CHO
5h 41m1 stop
$278Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
5:30 pm - 9:44 pmCHO-MDW
5h 14m1 stop
Delta Logo
10:35 am - 4:47 pmMDW-CHO
5h 12m1 stop
$307Delta
Find Deal
Mon, Nov 10 - Thu, Dec 4
Delta Logo
6:01 pm - 10:14 pmCHO-MDW
5h 13m1 stop
Delta Logo
5:04 pm - 11:00 pmMDW-CHO
4h 56m1 stop
$309Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
5:30 pm - 9:44 pmCHO-MDW
5h 14m1 stop
Delta Logo
10:35 am - 4:47 pmMDW-CHO
5h 12m1 stop
$314Delta
Find Deal
Wed, Nov 12 - Thu, Dec 4
Delta Logo
4:08 pm - 9:12 pmCHO-MDW
6h 04m1 stop
Delta Logo
6:04 am - 11:11 amMDW-CHO
4h 07m1 stop
$324Delta
Find Deal
Sat, Aug 16 - Tue, Aug 19
Delta Logo
5:30 pm - 9:44 pmCHO-MDW
5h 14m1 stop
Delta Logo
4:25 pm - 10:39 pmMDW-CHO
5h 14m1 stop
$353Delta
Find Deal
Mon, Nov 10 - Sat, Dec 6
Delta Logo
6:01 pm - 10:14 pmCHO-MDW
5h 13m1 stop
Delta Logo
10:35 am - 5:16 pmMDW-CHO
5h 41m1 stop
$354Delta
Find Deal
Fri, Oct 24 - Mon, Oct 27
Delta Logo
5:42 pm - 9:36 pmCHO-MDW
4h 54m1 stop
Delta Logo
10:35 am - 4:53 pmMDW-CHO
5h 18m1 stop
$439Delta
Find Deal
Wed, Sep 17 - Mon, Sep 22

Delta flights from Charlottesville to Chicago Midway Airport

Our best Delta deals on Charlottesville to Chicago Midway Airport flight tickets
Delta
Nov 11
CHO5:30 pmCharlottesville Albemarle
5h 14m
1 stop
MDW9:44 pmChicago Midway
Dec 2
MDW10:35 amChicago Midway
5h 12m
1 stop
CHO4:47 pmCharlottesville Albemarle
$229
Find similar
Delta
Nov 10
CHO5:30 pmCharlottesville Albemarle
5h 14m
1 stop
MDW9:44 pmChicago Midway
Dec 3
MDW10:35 amChicago Midway
5h 12m
1 stop
CHO4:47 pmCharlottesville Albemarle
$268
Find similar
Delta
Oct 23
CHO6:01 pmCharlottesville Albemarle
5h 13m
1 stop
MDW10:14 pmChicago Midway
Oct 27
MDW10:35 amChicago Midway
5h 41m
1 stop
CHO5:16 pmCharlottesville Albemarle
$278
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 August 2, 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

Tue 11/11

5:30 pm-9:44 pm

1 stop5h 14m

Chicago Midway

Tue 12/2

10:35 am-4:47 pm

1 stop5h 12m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 11/10

5:30 pm-9:44 pm

1 stop5h 14m

Chicago Midway

Wed 12/3

10:35 am-4:47 pm

1 stop5h 12m

$268

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/23

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Mon 10/27

10:35 am-5:16 pm

1 stop5h 41m

$278

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 11/10

5:30 pm-9:44 pm

1 stop5h 14m

Chicago Midway

Thu 12/4

10:35 am-4:47 pm

1 stop5h 12m

$307

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 10/23

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Mon 10/27

5:04 pm-11:00 pm

1 stop4h 56m

$309

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 11/12

5:30 pm-9:44 pm

1 stop5h 14m

Chicago Midway

Thu 12/4

10:35 am-4:47 pm

1 stop5h 12m

$314

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 8/16

4:08 pm-9:12 pm

1 stop6h 04m

Chicago Midway

Tue 8/19

6:04 am-11:11 am

1 stop4h 07m

$324

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 11/10

5:30 pm-9:44 pm

1 stop5h 14m

Chicago Midway

Sat 12/6

4:25 pm-10:39 pm

1 stop5h 14m

$353

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 10/24

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Mon 10/27

10:35 am-5:16 pm

1 stop5h 41m

$354

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/17

5:42 pm-9:36 pm

1 stop4h 54m

Chicago Midway

Mon 9/22

10:35 am-4:53 pm

1 stop5h 18m

$439

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 64% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 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

Best Price Found

$179

Fastest flight time

4h 48m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Charlottesville in the past 72 hours is $179. The best round-trip flight deal from Charlottesville to Chicago Midway Airport found on momondo in the last 72 hours is $229.
The fastest flight from Charlottesville to Chicago Midway Airport takes 4h 48m
There are no direct flights from Charlottesville to Chicago Midway Airport. Popular non-direct route for this connection is Charlottesville Albemarle Airport - 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 48m 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
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Hammond
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Crown Point
Munster
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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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