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Cheap flights from Charleston to Chicago from $44

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Charleston to Chicago departing on 2/25. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
5:15 am - 5:40 pm
ORD
-
CHS
11h 25m
1 stop
$105Spirit Airlines
Mon, Mar 2 - Thu, Mar 5
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
5:15 am - 5:40 pm
ORD
-
CHS
11h 25m
1 stop
$113Spirit Airlines
Tue, Mar 3 - Thu, Mar 5
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
5:15 am - 5:40 pm
ORD
-
CHS
11h 25m
1 stop
$117Spirit Airlines
Mon, Feb 23 - Thu, Feb 26
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
$121Spirit Airlines
Wed, Feb 18 - Sat, Feb 21
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
$129Spirit Airlines
Thu, Feb 19 - Fri, Feb 20
Multiple Airlines Logo
3:35 pm - 1:00 pm
CHS
-
MDW
22h 25m
1 stop
Multiple Airlines Logo
7:30 am - 2:40 pm
MDW
-
CHS
6h 10m
1 stop
$131Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
6:36 pm - 10:13 pm
ORD
-
CHS
26h 37m
1 stop
$137Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
Spirit Airlines Logo
6:35 pm - 9:13 pm
CHS
-
ORD
27h 38m
1 stop
Spirit Airlines Logo
6:51 pm - 4:05 pm
ORD
-
CHS
20h 14m
1 stop
$144Spirit Airlines
Mon, Feb 23 - Fri, Feb 27
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
$145Spirit Airlines
Thu, Feb 19 - Fri, Feb 20
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
$146Spirit Airlines
Mon, Mar 2 - Mon, Mar 9

Spirit Airlines flights from Charleston to Chicago

Our best Spirit Airlines deals on Charleston to Chicago flight tickets
Spirit Airlines
Feb 18
CHS5:00 pmCharleston
8h 40m
1 stop
ORD12:40 amChicago O'Hare Intl
Feb 21
ORD7:00 amChicago O'Hare Intl
9h 40m
1 stop
CHS5:40 pmCharleston
$121
Spirit Airlines
Feb 19
CHS5:00 pmCharleston
8h 40m
1 stop
ORD12:40 amChicago O'Hare Intl
Feb 20
ORD7:00 amChicago O'Hare Intl
9h 40m
1 stop
CHS5:40 pmCharleston
$129
Spirit Airlines
Feb 28
CHS5:00 pmCharleston
8h 40m
1 stop
ORD12:40 amChicago O'Hare Intl
Mar 3
ORD6:51 pmChicago O'Hare Intl
20h 14m
1 stop
CHS4:05 pmCharleston
$134

Southwest flights from Charleston to Chicago

Our best Southwest deals on Charleston to Chicago flight tickets
Southwest
Apr 8
CHS12:00 pmCharleston
5h 45m
1 stop
MDW4:45 pmChicago Midway
Apr 11
MDW3:30 pmChicago Midway
2h 05m
CHS6:35 pmCharleston
$295
Southwest
May 5
CHS7:15 amCharleston
2h 15m
MDW8:30 amChicago Midway
May 9
MDW3:30 pmChicago Midway
2h 05m
CHS6:35 pmCharleston
$299
Southwest
Apr 8
CHS1:15 pmCharleston
7h 55m
2 stops
MDW8:10 pmChicago Midway
Apr 11
MDW3:30 pmChicago Midway
2h 05m
CHS6:35 pmCharleston
$300

momondo Fare Finder

 
Customize your flight search to find flights from Charleston to Chicago 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 February 5, 2026.
Use the filters below to find and compare flights from Charleston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Mon 3/2

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Thu 3/5

5:15 am-5:40 pm

1 stop11h 25m

$105

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Tue 3/3

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Thu 3/5

5:15 am-5:40 pm

1 stop11h 25m

$113

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Mon 2/23

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Thu 2/26

5:15 am-5:40 pm

1 stop11h 25m

$117

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 2/18

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Sat 2/21

7:00 am-5:40 pm

1 stop9h 40m

$121

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 2/19

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Fri 2/20

7:00 am-5:40 pm

1 stop9h 40m

$129

CharlestonChicago

CHS - MDW

CHSMDW

Charleston

Tue 5/5

3:35 pm-1:00 pm

1 stop22h 25m

Chicago Midway

Sat 5/9

7:30 am-2:40 pm

1 stop6h 10m

$131

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Wed 3/4

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Wed 3/11

6:36 pm-10:13 pm

1 stop26h 37m

$137

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Mon 2/23

6:35 pm-9:13 pm

1 stop27h 38m

Chicago O'Hare Intl

Fri 2/27

6:51 pm-4:05 pm

1 stop20h 14m

$144

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Thu 2/19

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Fri 2/20

7:00 am-5:40 pm

1 stop9h 40m

$145

CharlestonChicago

CHS - ORD

CHSORD

Charleston

Mon 3/2

5:00 pm-12:40 am

1 stop8h 40m

Chicago O'Hare Intl

Mon 3/9

7:00 am-5:40 pm

1 stop9h 40m

$146

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 Charleston to Chicago

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 typical price of a round-trip flight between Charleston and Chicago?

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Charleston, with most prices found around $284. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Charleston to Chicago during September average around $310.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $401. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Charleston to Chicago for around $649.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Charleston to Chicago during this time can be as low as $378. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.

What is the cheapest Charleston to Chicago flight route?

Fly from Charleston to Chicago O'Hare Intl for the best Charleston - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Charleston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $372 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Charleston for as low as $268 on momondo.

What cabin class options are available on Charleston to Chicago flights?

There are 4 cabin classes available to choose from on Charleston to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Charleston to Chicago flight prices changed over time?

As of February 2026, prices for Charleston to Chicago flights are approximately 5% cheaper when compared to flights at the same time last year.

When to book flights from Charleston to Chicago

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

Cheap Charleston to Chicago (CHS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charleston to Chicago

Best Price Found

$181

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Charleston in the past 72 hours is $181. The best round-trip flight deal from Charleston to Chicago found on momondo in the last 72 hours is $369.
The fastest flight from Charleston to Chicago takes 2h 10m
Direct flights go from Charleston to Chicago every day.
There are 3 airports in Chicago. From Charleston there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • How far is Charleston to Chicago by plane?

    Chicago is 756.4 mi away from Charleston. By plane, this route typically takes 2h 10m.

  • When did momondo last update prices for flights from Charleston Airport to Chicago?

    Prices for flights from Charleston Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Charleston Airport to Chicago?

  • How old do you have to be to fly from Charleston Airport to Chicago?

    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 Charleston Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Charleston to Chicago?

  • What is the most popular airline from Charleston to Chicago?

Best airlines flying from Charleston to Chicago

Compare and see reviews for airlines that fly from Charleston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $135Free CancellationRating
7.2
11,237 reviews
Search American Airlines flights
SouthwestPriceFrom $190Free CancellationRating
8.0
4,275 reviews
Search Southwest flights
DeltaPriceFrom $233Free CancellationRating
7.9
8,151 reviews
Search Delta flights
United AirlinesPriceFrom $237Free CancellationRating
7.4
9,240 reviews
Search United Airlines flights

  • Southwest Flights From Charleston to Chicago

    Southwest flight deals from Charleston to Chicago start from $190 round-trip. Over the 3 Southwest flights for this route in a normal week, average airfare is usually $381 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Charleston to Chicago

    Across 9,240 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Charleston to Chicago about 18 times each week, with ticket deals ranging from $237 to $391. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Charleston 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 Charleston to Chicago with flexible booking policies on momondo?

All flight searches from Charleston to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

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

Yes. momondo can track prices for Charleston to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport