Chicago from Charleston, Oct 16–18: round trip from $547
When we checked, nonstop round-trip flights on American from Charleston to Chicago were $547 per person, or $1,094 for two, for Oct 16–18, 2026 (2 nights). Highs run 52–62°F, with a 60% chance of rain on Friday and clear skies after that. The best-value hotel, Club Quarters Hotel Central Loop, Chicago, is $893 for the stay.
The flight
$547 per person, round trip
$1,094 for two, taxes and fees included · American · nonstop · 2h 43m
Out Fri, Oct 16, 7:16 AM – Fri, Oct 16, 8:59 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American | $547 | nonstop | 2h 43m |
| United | $567 | nonstop | 2h 30m |
| American | $547 | nonstop | 2h 44m |
Prices checked Oct 12, 2026, 9:45 PM EDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $1,094 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights | $893 |
| Trip total for two | $1,987 |
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Why go now
The fare is $547 per person round trip, nonstop. The median of 11 earlier checks on this route is $569, so this one is $22 less, or 4%. It isn't the lowest we've seen, since one recent check came in at $507, but it's a solid nonstop price. For $1,094 for two, the 7:16 AM American flight lands at O'Hare at 8:59 AM local time, so you still get all of Friday. Add the best-value hotel at $893 and $520 of spending money and the weekend comes to $2,507 for two. Friday looks overcast with a 60% chance of rain and a high of 56°F. Saturday looks mostly clear at 52°F, and Sunday clear at 62°F. That's good weather for jacket-on city days: a museum while it rains, then a river cruise and deep-dish once it clears.
The kind of trip this is
This is a fall city getaway built on architecture, museums, food and nightlife. It suits a couple or a pair of friends who like to walk a lot, eat well and stay out for live music. The pace is full but easy: two nights, one hotel in the Loop, and most of the big sights close enough to walk to. It's a long weekend that runs on sightseeing by day and blues clubs and pizza at night.
Weather in Chicago, Oct 16–18
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 60% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
All three picks are 4-star hotels in The Loop, which puts the architecture, the theaters and Millennium Park right at your door. Club Quarters Hotel Central Loop, Chicago is the best value: $893 for the 2 nights ($447 a night) for a Club Room, rated 8.2 across 5,337 reviews. Canopy By Hilton Chicago Central Loop is the top rated at 8.9 from 308 reviews, at $962 for the stay ($481 a night) for a King Room - Mobility Access. Congress Plaza Hotel Chicago is the budget pick at $750 ($375 a night) for a King Room, rated 7.1. It's also the only one of the three with free cancellation. All three rates are room only. If nightlife is the plan, River North is the area for galleries, steakhouses and late nights.
Club Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 a night
See roomsCanopy By Hilton Chicago Central Loop
$962 for 2 nights, two guests · $481 a night
See roomsCongress Plaza Hotel Chicago
$750 for 2 nights, two guests · $375 a night
See roomsAll hotels in Chicago for these dates
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Where in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise on clear, dry Saturday.
- See the Bean and the fountains in Millennium Park, a short walk from all three hotels.
- Spend rainy Friday inside the Art Institute of Chicago.
- Eat deep-dish at Lou Malnati's or Pequod's and settle the debate yourselves.
- Hear live blues at Kingston Mines on Saturday night.
- Catch a Cubs game at Wrigley Field if the schedule lines up.
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Charleston | Charleston International (CHS) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 43m nonstop |
| Distance | 757 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,094 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $893 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,507 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: Charleston to Chicago
| Per person | |
|---|---|
| This trip | $547 per person |
| Lowest in the last 30 days | $507 (Oct 13, 2026) |
| Typical price, last 60 days | $569 |
| Price checks | 11 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars.
- Chicago is 1 hour behind Charleston. The nonstop covers 757 miles in about 2h 43m.
- All three hotel rates are room only. Only Congress Plaza Hotel Chicago offers free cancellation.
- Prices are all-in, with taxes and fees included, as found when we checked. They can change before you book.
- Chicago has two airports, O'Hare (ORD) and Midway (MDW). The fare we found flies into O'Hare.
Questions readers ask
How much is the flight?
When we checked, it was $547 per person round trip, or $1,094 for two, nonstop on American from Charleston to O'Hare. A United nonstop was $567 per person.
What time does it leave?
The American flight leaves Charleston at 7:16 AM on Friday, Oct 16, and lands at 8:59 AM Chicago time. There's also a 3:53 PM departure at the same fare that lands at 5:37 PM.
What is the weather like?
The forecast for Friday is overcast with a high of 56°F and a 60% chance of rain. Saturday looks mostly clear at 52°F, and Sunday clear at 62°F. Lows sit between 44°F and 46°F, so pack a warm layer.
What does the whole weekend cost for two?
About $2,507 for two: $1,094 for flights, $893 for the best-value hotel and $520 for spending, which works out to $130 per person per day.
Is 2 nights enough?
For a first look, yes. The morning flight gives you most of Friday, and from a Loop hotel you can walk to Millennium Park and the Art Institute. You'd have time for a river cruise, deep-dish and a blues night.
Do I need a passport?
No. It's a domestic flight, and Chicago uses the US dollar.
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Image credits
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