CRW - CHI

$187 Find Cheap Flights from Charleston to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$309
Typical prices: $266-$437
United Airlines
Mon 1/15Fri 1/19
CRW - ORD • Non-stop
Cheapest non-stop
$309
Typical prices: $261-$434
United Airlines
Sat 4/7Sat 4/14
CRW - ORD • Non-stop
Nonstop flights
Every day
You can fly direct with United Airlines. Average duration is 2h 07m
Direct flights
+1
Direct flights
+1
Top routes
CRW - MDW
Cheapest • 12% average savings
CRW - ORD
Most popular
Insights
Insights
When to travel
September
Cheapest • 26% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $264 (round-trip)
Charlotte Douglas (CLT)
Shortest trip • 5h 01m (one-way)
Insights
Insights
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Booking Insights
Flight Deals

Cheap Flights from Charleston to Chicago (CRW-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charleston to Chicago

Thu, Nov 12 - Sun, Nov 15
United Airlines Logo
6:02 am - 7:05 amCRW  Charleston Yeager-ORD Chicago O'Hare Intl
2h 03mnonstop
United Airlines Logo
10:25 am - 1:15 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
1h 50mnonstop
$309United Airlines
Fri, Jan 15 - Tue, Jan 19
United Airlines Logo
10:35 am - 11:44 amCRW  Charleston Yeager-ORD Chicago O'Hare Intl
2h 09mnonstop
United Airlines Logo
2:35 pm - 5:27 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
1h 52mnonstop
$309United Airlines
Wed, Apr 7 - Wed, Apr 14
United Airlines Logo
1:50 pm - 2:49 pmCRW  Charleston Yeager-ORD Chicago O'Hare Intl
1h 59mnonstop
United Airlines Logo
10:25 am - 1:13 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
1h 48mnonstop
$309United Airlines
Thu, Dec 3 - Sun, Dec 6
American Airlines Logo
11:04 am - 5:29 pmCRW  Charleston Yeager-ORD Chicago O'Hare Intl
7h 25m1 stop Charlotte Douglas
American Airlines Logo
8:10 am - 2:26 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
5h 16m1 stop Charlotte Douglas
$328American Airlines
Fri, Jan 15 - Tue, Jan 19
American Airlines Logo
6:00 am - 11:03 amCRW  Charleston Yeager-ORD Chicago O'Hare Intl
6h 03m1 stop Charlotte Douglas
American Airlines Logo
12:03 pm - 6:44 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
5h 41m1 stop Charlotte Douglas
$328American Airlines
Wed, Mar 24 - Tue, Mar 30
Delta Logo
6:40 pm - 10:20 pmCRW  Charleston Yeager-ORD Chicago O'Hare Intl
4h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 2:41 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
4h 11m1 stop Atlanta Hartsfield-Jackson
$328Delta
Wed, Apr 7 - Wed, Apr 14
Delta Logo
6:00 am - 10:02 amCRW  Charleston Yeager-ORD Chicago O'Hare Intl
5h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:10 am - 5:53 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
5h 43m1 stop Atlanta Hartsfield-Jackson
$328Delta
Fri, Nov 13 - Sun, Nov 15
American Airlines Logo
7:04 pm - 12:01 amCRW  Charleston Yeager-ORD Chicago O'Hare Intl
5h 57m1 stop Charlotte Douglas
American Airlines Logo
6:41 am - 2:22 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
6h 41m1 stop Charlotte Douglas
$328American Airlines
Fri, Nov 13 - Sun, Nov 15
Delta Logo
6:00 am - 10:25 amCRW  Charleston Yeager-ORD Chicago O'Hare Intl
5h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:49 am - 1:53 pmORD  Chicago O'Hare Intl-CRW Charleston Yeager
6h 04m1 stop Atlanta Hartsfield-Jackson
$328Delta
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
11:04 am - 5:29 pmCRW  Charleston Yeager-ORD Chicago O'Hare Intl
7h 25m1 stop Charlotte Douglas
American Airlines Logo
5:23 am - 11:57 amORD  Chicago O'Hare Intl-CRW Charleston Yeager
5h 34m1 stop Charlotte Douglas
$328American Airlines
Booking Insights

Price, demand and travel trends for Charleston to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Charleston to Chicago?

Round-trip flights from Charleston to Chicago typically range from $266 to $437. The lowest price found in the past 5 days was $309, on United Airlines.

What is the cheapest Charleston to Chicago flight route?

Charleston (CRW) to Chicago Midway Airport (MDW) is the cheapest Charleston to Chicago route, averaging $268 round-trip. Other Charleston to Chicago routes average $343, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Charleston to Chicago?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Charleston to Chicago. It’s 15% cheaper than the average day, while Tuesday is the most expensive, with prices 82% higher.

What’s the cheapest month to fly from Charleston to Chicago?

•September is the cheapest month to fly from Charleston to Chicago at $252 round-trip.
•October ($445) and June ($392) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 76% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Charleston to Chicago flights

Low season

February

Cheapest flight

$187
Beat the crowds with an average 38% drop in travelers.
The most popular month to fly with an average 37% increase in travelers.
One-way flight from Charleston to Chicago O'Hare Intl Airport

When to book flights from Charleston to Chicago

Are your dates flexible? Find out the best times to travel from Charleston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Charleston to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Charleston to Chicago?

    These are the earliest and latest flight times available from Charleston to Chicago:

    • Earliest: departs at 5:00 am and lands at 7:07 am
    • Latest: departs at 7:10 pm and lands at 9:17 pm.

    The flight takes about 2h 07m.

  • What cabin classes can I book on flights from Charleston to Chicago?

    Two cabin classes are available on flights from Charleston to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Charleston to Chicago?

    A nonstop flight from Charleston to Chicago takes 2h 07m, covering 400 miles.

  • Do I need a passport to fly from Charleston to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Charleston to Chicago flight?

    Round-trip flights from Charleston to Chicago range from $266 to $437, with an average of $341 over the past 12 months. Anything below $266 counts as a good deal.

  • How much can I save by taking a layover when flying from Charleston to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $264 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $344 for nonstop.

  • What is the standard checked-bag allowance on flights from Charleston to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$80 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Charleston to Chicago spread across the day?

    Morning is the busiest departure period on Charleston to Chicago flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Charleston to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $309 to $2,455. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Charleston to Chicago looking right now?

    One-way fares from Charleston to Chicago are currently lower than usual. Average one-way flight prices are about $251, which is 5% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Charleston to Chicago?

    Flights from Charleston to Chicago usually depart from Charleston Yeager (CRW) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Charleston to Chicago pass through?

    Connecting flights from Charleston to Chicago most commonly pass through:

    • Charlotte Douglas (CLT) - 77% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 23% of one-stop connections

  • Can I save money by using flexible dates for flights from Charleston to Chicago?

    Yes. Flexible dates can save you up to 54% on flights from Charleston to Chicago. Wednesday is the cheapest departure day at $292 round-trip on average, while Tuesday is the most expensive at $622, a difference of $330.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Charleston to Chicago?

    Only United Airlines operates flights between Charleston and Chicago.

  • How much time can I save by choosing a different layover airport from Charleston to Chicago?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 5h 01m, compared with 5h 06m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Charleston and Chicago?

    Chicago is 1 hour behind Charleston (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Charleston to Chicago flights?

    Among airlines operating Charleston to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Charleston to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Charleston to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Tuesday. On this route, Wednesday flights average $292, about $330 less than Tuesday fares (53% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Charleston to Chicago trip for September. Fares historically average $252 round-trip in that month - typically $193 less than the most expensive month, which is October (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $264 round-trip on this route - about $79 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

Prefer to fly direct from Charleston to Chicago?

 
Find which airlines fly direct from Charleston Yeager Airport to Chicago, which days they fly and book direct flights.

Direct departures

Charleston Yeager to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Charleston Yeager

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

More options for your flight from Charleston to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
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