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Cheap flights from Chicago Midway Airport to Charlottesville 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 Chicago Midway Airport to Charlottesville departing on 5/29. 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
0 bags

Find the cheapest flights from Chicago Midway Airport to Charlottesville

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 11:25 am
MDW
-
CHO
4h 25m
1 stop
Delta Logo
6:00 am - 10:09 am
CHO
-
MDW
5h 09m
1 stop
$289Delta
Wed, Jun 10 - Wed, Jun 17
Delta Logo
6:23 am - 1:46 pm
MDW
-
CHO
6h 23m
1 stop
Delta Logo
5:39 pm - 9:09 pm
CHO
-
MDW
4h 30m
1 stop
$309Delta
Tue, May 19 - Tue, May 26
Delta Logo
6:05 am - 11:27 am
MDW
-
CHO
4h 22m
1 stop
Delta Logo
6:00 am - 10:03 am
CHO
-
MDW
5h 03m
1 stop
$344Delta
Thu, Jul 9 - Sun, Jul 12
Delta Logo
6:05 am - 1:52 pm
MDW
-
CHO
6h 47m
1 stop
Delta Logo
6:00 am - 10:03 am
CHO
-
MDW
5h 03m
1 stop
$354Delta
Thu, Jul 9 - Sun, Jul 12
Delta Logo
5:08 pm - 11:44 pm
MDW
-
CHO
5h 36m
1 stop
Delta Logo
6:00 am - 10:00 am
CHO
-
MDW
5h 00m
1 stop
$384Delta
Fri, May 29 - Sun, May 31
Delta Logo
6:05 am - 1:52 pm
MDW
-
CHO
6h 47m
1 stop
Delta Logo
6:00 am - 10:03 am
CHO
-
MDW
5h 03m
1 stop
$394Delta
Thu, Jul 9 - Sun, Jul 12
Delta Logo
6:05 am - 11:27 am
MDW
-
CHO
4h 22m
1 stop
Delta Logo
5:37 pm - 10:15 pm
CHO
-
MDW
5h 38m
1 stop
$399Delta
Fri, Jul 17 - Fri, Jul 24
Delta Logo
4:30 pm - 11:35 pm
MDW
-
CHO
6h 05m
1 stop
Delta Logo
6:00 am - 10:00 am
CHO
-
MDW
5h 00m
1 stop
$404Delta
Sun, May 24 - Sun, May 31
Delta Logo
6:05 am - 11:27 am
MDW
-
CHO
4h 22m
1 stop
Delta Logo
4:02 pm - 10:15 pm
CHO
-
MDW
7h 13m
1 stop
$414Delta
Thu, Aug 6 - Sat, Aug 8
Delta Logo
10:35 am - 4:49 pm
MDW
-
CHO
5h 14m
1 stop
Delta Logo
6:00 am - 9:50 am
CHO
-
MDW
4h 50m
1 stop
$424Delta
Fri, Sep 4 - Sun, Sep 6

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Delta flights from Chicago Midway Airport to Charlottesville

Our best Delta deals on Chicago Midway Airport to Charlottesville flight tickets
Delta
Jun 10
MDW6:00 amChicago Midway
4h 25m
1 stop
CHO11:25 amCharlottesville Albemarle
Jun 17
CHO6:00 amCharlottesville Albemarle
5h 09m
1 stop
MDW10:09 amChicago Midway
$289
Delta
May 19
MDW6:23 amChicago Midway
6h 23m
1 stop
CHO1:46 pmCharlottesville Albemarle
May 26
CHO5:39 pmCharlottesville Albemarle
4h 30m
1 stop
MDW9:09 pmChicago Midway
$309
Delta
Jul 9
MDW6:05 amChicago Midway
4h 22m
1 stop
CHO11:27 amCharlottesville Albemarle
Jul 12
CHO6:00 amCharlottesville Albemarle
5h 03m
1 stop
MDW10:03 amChicago Midway
$344

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Charlottesville 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 April 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Charlottesville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Wed 6/10

6:00 am-11:25 am

1 stop4h 25m

Charlottesville Albemarle

Wed 6/17

6:00 am-10:09 am

1 stop5h 09m

$289

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Tue 5/19

6:23 am-1:46 pm

1 stop6h 23m

Charlottesville Albemarle

Tue 5/26

5:39 pm-9:09 pm

1 stop4h 30m

$309
Quickest round-trip

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Thu 7/9

6:05 am-11:27 am

1 stop4h 22m

Charlottesville Albemarle

Sun 7/12

6:00 am-10:03 am

1 stop5h 03m

$344

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Thu 7/9

6:05 am-1:52 pm

1 stop6h 47m

Charlottesville Albemarle

Sun 7/12

6:00 am-10:03 am

1 stop5h 03m

$354

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Fri 5/29

5:08 pm-11:44 pm

1 stop5h 36m

Charlottesville Albemarle

Sun 5/31

6:00 am-10:00 am

1 stop5h 00m

$384

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Thu 7/9

6:05 am-1:52 pm

1 stop6h 47m

Charlottesville Albemarle

Sun 7/12

6:00 am-10:03 am

1 stop5h 03m

$394

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Fri 7/17

6:05 am-11:27 am

1 stop4h 22m

Charlottesville Albemarle

Fri 7/24

5:37 pm-10:15 pm

1 stop5h 38m

$399

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Sun 5/24

4:30 pm-11:35 pm

1 stop6h 05m

Charlottesville Albemarle

Sun 5/31

6:00 am-10:00 am

1 stop5h 00m

$404

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Thu 8/6

6:05 am-11:27 am

1 stop4h 22m

Charlottesville Albemarle

Sat 8/8

4:02 pm-10:15 pm

1 stop7h 13m

$414

ChicagoCharlottesville

MDW - CHO

MDWCHO

Chicago Midway

Fri 9/4

10:35 am-4:49 pm

1 stop5h 14m

Charlottesville Albemarle

Sun 9/6

6:00 am-9:50 am

1 stop4h 50m

$424

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to Charlottesville

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 day to depart on your flight to Charlottesville?

The cheapest day to depart from Chicago Midway Airport to Charlottesville is on a Wednesday. Travelers who choose to depart for Charlottesville on a Wednesday will often find tickets for as low as $364. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $557.

What is the cheapest time of day to depart on your flight to Charlottesville?

Flying to Charlottesville from Chicago Midway Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $375 when looking at flights departing in the morning. Flights in the evening are often more expensive with an average ticket price of $489.

When to book flights from Chicago Midway Airport to Charlottesville

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

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

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

Fastest flight time

4h 16m

Direct flights

None
The fastest flight from Chicago Midway Airport to Charlottesville takes 4h 16m
There are no direct flights from Chicago Midway Airport to Charlottesville. There are no popular flight routes from Chicago Midway Airport to Charlottesville.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Charlottesville

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

    A flight from Chicago Midway to Charlottesville Albemarle will travel around 554.6 mi. Flights usually cover this in 4h 16m, depending on flying conditions and air traffic around both airports.

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

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

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

  • What documentation or ID do you need to fly to Charlottesville Albemarle Airport?

    The required travel and health documents for your Charlottesville Albemarle Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Charlottesville Albemarle Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Charlottesville?

Book flights to Charlottesville if you plan to visit one of these locations
Orange
Keswick

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Charlottesville. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for Chicago to Charlottesville flights to just show those with flexible booking policies.

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

Once you have performed a search for Chicago to Charlottesville 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 Chicago to Charlottesville right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Charlottesville now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Charlottesville and let you know when they change.

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