Latest deals
Insights
When to book
FAQs
Price Alerts

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 5/23. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Charlottesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:50 am - 3:27 pm
CHO
-
MDW
4h 37m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
CHO
7h 29m
1 stop
$289Delta
Wed, Sep 9 - Sat, Sep 12
Delta Logo
5:39 pm - 9:09 pm
CHO
-
MDW
4h 30m
1 stop
Delta Logo
6:23 am - 1:46 pm
MDW
-
CHO
6h 23m
1 stop
$344Delta
Thu, May 28 - Sun, May 31
Delta Logo
3:05 pm - 9:46 pm
CHO
-
MDW
7h 41m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
CHO
7h 29m
1 stop
$384Delta
Wed, Sep 16 - Mon, Sep 21
Delta Logo
5:54 pm - 10:28 pm
CHO
-
MDW
5h 34m
1 stop
Delta Logo
5:21 pm - 10:55 pm
MDW
-
CHO
4h 34m
1 stop
$404Delta
Tue, Apr 14 - Sat, Apr 18
Delta Logo
5:36 pm - 10:17 pm
CHO
-
MDW
5h 41m
1 stop
Delta Logo
6:05 am - 11:25 am
MDW
-
CHO
4h 20m
1 stop
$434Delta
Tue, Jun 9 - Sun, Jun 14
Delta Logo
5:54 pm - 10:28 pm
CHO
-
MDW
5h 34m
1 stop
Delta Logo
5:21 pm - 10:55 pm
MDW
-
CHO
4h 34m
1 stop
$444Delta
Mon, Apr 13 - Mon, Apr 20
Delta Logo
5:54 pm - 10:28 pm
CHO
-
MDW
5h 34m
1 stop
Delta Logo
5:21 pm - 10:55 pm
MDW
-
CHO
4h 34m
1 stop
$494Delta
Tue, Apr 14 - Sat, Apr 18
Delta Logo
5:39 pm - 9:09 pm
CHO
-
MDW
4h 30m
1 stop
Delta Logo
5:12 pm - 11:44 pm
MDW
-
CHO
5h 32m
1 stop
$504Delta
Fri, May 22 - Tue, May 26
Delta Logo
5:54 pm - 10:28 pm
CHO
-
MDW
5h 34m
1 stop
Delta Logo
6:00 am - 11:17 am
MDW
-
CHO
4h 17m
1 stop
$514Delta
Thu, Apr 23 - Sun, Apr 26
Delta Logo
6:00 am - 10:03 am
CHO
-
MDW
5h 03m
1 stop
Delta Logo
6:05 am - 11:27 am
MDW
-
CHO
4h 22m
1 stop
$549Delta
Fri, Aug 7 - Sun, Aug 9

Delta flights from Charlottesville to Chicago Midway Airport

Our best Delta deals on Charlottesville to Chicago Midway Airport flight tickets
Delta
Sep 9
CHO11:50 amCharlottesville Albemarle
4h 37m
1 stop
MDW3:27 pmChicago Midway
Sep 12
MDW6:00 amChicago Midway
7h 29m
1 stop
CHO2:29 pmCharlottesville Albemarle
$289
Delta
May 28
CHO5:39 pmCharlottesville Albemarle
4h 30m
1 stop
MDW9:09 pmChicago Midway
May 31
MDW6:23 amChicago Midway
6h 23m
1 stop
CHO1:46 pmCharlottesville Albemarle
$344
Delta
Sep 16
CHO3:05 pmCharlottesville Albemarle
7h 41m
1 stop
MDW9:46 pmChicago Midway
Sep 21
MDW6:00 amChicago Midway
7h 29m
1 stop
CHO2:29 pmCharlottesville Albemarle
$384

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 March 28, 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 9/9

11:50 am-3:27 pm

1 stop4h 37m

Chicago Midway

Sat 9/12

6:00 am-2:29 pm

1 stop7h 29m

$289

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 5/28

5:39 pm-9:09 pm

1 stop4h 30m

Chicago Midway

Sun 5/31

6:23 am-1:46 pm

1 stop6h 23m

$344

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/16

3:05 pm-9:46 pm

1 stop7h 41m

Chicago Midway

Mon 9/21

6:00 am-2:29 pm

1 stop7h 29m

$384

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 4/14

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sat 4/18

5:21 pm-10:55 pm

1 stop4h 34m

$404

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 6/9

5:36 pm-10:17 pm

1 stop5h 41m

Chicago Midway

Sun 6/14

6:05 am-11:25 am

1 stop4h 20m

$434

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Mon 4/13

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Mon 4/20

5:21 pm-10:55 pm

1 stop4h 34m

$444

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 4/14

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sat 4/18

5:21 pm-10:55 pm

1 stop4h 34m

$494

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 5/22

5:39 pm-9:09 pm

1 stop4h 30m

Chicago Midway

Tue 5/26

5:12 pm-11:44 pm

1 stop5h 32m

$504

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 4/23

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sun 4/26

6:00 am-11:17 am

1 stop4h 17m

$514
Quickest round-trip

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 8/7

6:00 am-10:03 am

1 stop5h 03m

Chicago Midway

Sun 8/9

6:05 am-11:27 am

1 stop4h 22m

$549

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 69% 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

  • 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
Schererville
Munster
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 4/27
Mon 5/4
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago