Charleston to Chicago: what the flight costs
In the last 60 days we checked this route 22 times. The typical return was £506 per person and the lowest £382, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £382 |
| Typical (median) | £506 |
| Price checks, 60 days | 22 |
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Trips we picked on this route
Next weekend · from Charleston
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on American, 2h 43m, landing at 8:59 AM Friday
- $547 per person, $22 below the $569 typical fare
- Clear Saturday and Sunday, highs 52°F and 62°F, 1% rain
£1,498 for two · 2 nights · flights, hotel, taxes & fees
Flights £825 + hotel £673, taxes in · a checked bag each adds about £121
American · nonstop · 2h 43m
The catch: Friday has a 60% chance of rain, the value hotel has no free cancellation, and resort fees and a checked bag aren't in the total.
Worth it if you want a quick city weekend of architecture, art and deep-dish; skip it if you need a refundable room at the value hotel.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 15 Oct 2026 | 23 – 25 Oct 2026 | £540 | UA | nonstop | 2h 32m | Kiwi.com |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £547 | UA | with a stop | 6h 55m | Kiwi.com |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £421 | JetBlue | with a stop | 5h 40m | Google Flights |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £571 | MX + F9 | with a stop | 35h 23m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £421 | JetBlue | with a stop | 5h 40m | Google Flights |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £455 | B6 + F9 + MX | with a stop | 5h 40m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £506 | B6 + F9 + MX | with a stop | 5h 40m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £515 | B6 | with a stop | 29h 57m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £421 | JetBlue | with a stop | 5h 40m | Google Flights |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £540 | UA | nonstop | 2h 32m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £506 | B6 + F9 + MX | with a stop | 5h 40m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £412 | American | nonstop | 2h 43m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £382 | MX + F9 | with a stop | 36h 23m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £531 | UA | with a stop | 7h 2m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £412 | American | nonstop | 2h 43m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £421 | B6 + F9 + MX | with a stop | 5h 40m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £524 | UA | nonstop | 2h 32m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £512 | UA | nonstop | 2h 32m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £531 | UA | with a stop | 7h 2m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £412 | United | nonstop | 2h 30m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £429 | B6 + F9 + MX | with a stop | 5h 40m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £524 | UA | nonstop | 2h 32m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Charleston to Chicago
What does a return from Charleston to Chicago usually cost?
Over the last 60 days the typical price we found was £506 per person, taxes and fees included, across 22 checks; the lowest was £382.
When is the best time to fly from Charleston to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Charleston to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.