Chicago from Charleston, 16 – 18 Oct: £1,498 for two, all in
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The verdict
Our verdict
Worth it, because
- 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
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.
Worth it for the two of you: $1,987 for two, all in. That's the flights at $1,094 plus 2 nights at Club Quarters Hotel Central Loop, Chicago at $893, taxes and fees included, for Friday, Oct 16 to Sunday, Oct 18, 2026, nonstop on American from Charleston to O'Hare in 2h 43m. Resort fees, a checked bag and spending money are not in that total.
The total, before you go
£1,498 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £825 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £673 |
| The total, before you go | £1,498 |
| Hold luggage each, return (not in the total) | about £121 |
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on American, £121 for two return); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£412 per person, return
£825 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 | £412 | nonstop | 2h 43m |
| United | £427 | nonstop | 2h 30m |
| American | £412 | nonstop | 2h 44m |
Prices checked 12 Oct 2026, 21:45 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $547 per person, this nonstop is $22 below the $569 typical fare from our earlier checks on this route, or 4% under. With the hotel, the whole weekend comes to $1,987 for two. You leave Charleston at 7:16 AM on Friday, Oct 16 and land at O'Hare at 8:59 AM, so you get most of Friday in the city. Mid-October means jacket weather. Friday looks overcast with a high of 56°F and a 60% chance of rain. Then Saturday clears up with a high of 52°F and Sunday reaches 62°F, both with a 1% chance of rain. That's two dry days for the river cruise and Millennium Park. Heads-up: this fare was $507 in an earlier check, so it has already moved, and we can't say where it goes next.
The kind of trip this is
This is a city weekend built around walking: skyscraper architecture from the river, the Art Institute, deep-dish for dinner and live blues late. It suits a couple or two friends who like to keep moving and eat well. Staying in the Loop keeps most of it close, so the pace can be full without feeling rushed. Pack layers for cool October days.
Weather in Chicago, 16 – 18 Oct
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 56 °F | 46 °F | 60% |
| Sat 17 Oct | 52 °F | 44 °F | 1% |
| Sun 18 Oct | 62 °F | 45 °F | 1% |
Where to stay in Chicago
All three hotels are in The Loop, which puts the architecture, the theatres and Millennium Park at your doorstep. Club Quarters Hotel Central Loop, Chicago is our value pick and the one in the total: $893 for the 2 nights ($447 a night) for a Club Room, rated 8.2 from 5,337 reviews, with no free cancellation. Canopy By Hilton Chicago Central Loop is the top-rated pick at 8.9 from 308 reviews, $962 for the stay ($481 a night), also with no free cancellation. Congress Plaza Hotel Chicago is the budget pick at $750 for the stay ($375 a night), rated 7.1 from 4,548 reviews, and it's the only one of the three with free cancellation. All three are room only.
Club Quarters Hotel Central Loop, Chicago
£673 for 2 nights, two guests · £337 a night
See roomsCanopy By Hilton Chicago Central Loop
£725 for 2 nights, two guests · £363 a night
See roomsCongress Plaza Hotel Chicago
£565 for 2 nights, two guests · £283 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 Saturday
- See the Bean and the fountains in Millennium Park, a short walk from the Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend rainy Friday inside the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if one is on
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 | £825 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £673 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,890 |
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 | £412 per person |
| Lowest in the last 30 days | £382 (13 Oct 2026) |
| Typical price, last 60 days | £429 |
| Price checks | 11 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, and you pay in US dollars.
- Chicago is 1 hour behind Charleston.
- The nonstop covers 757 miles in 2h 43m, from Charleston International (CHS) to Chicago O'Hare International (ORD).
- Prices are all-in as found when we checked, and none of them is promised to hold.
- We'd budget $520 in spending money for two, which brings the weekend to $2,507.
Questions readers ask
Is it worth it?
Yes, for the two of you. It's a 2h 43m nonstop at $547 per person, $22 below the $569 typical fare, and the forecast shows two clear days. The trade-offs are rain on Friday and no free cancellation at the value hotel.
How much is the whole trip for two?
$1,987 for two, all in: $1,094 for the flights and $893 for 2 nights at Club Quarters Hotel Central Loop, Chicago, taxes and fees included. Resort fees, a checked bag and spending money aren't in it. With $520 of spending money, the weekend comes to $2,507.
What is the weather like?
Friday, Oct 16 looks overcast with a high of 56°F and a 60% chance of rain. Saturday is mostly clear with a high of 52°F, and Sunday is clear at 62°F, both with a 1% chance of rain. Lows run 44°F to 46°F.
Is 2 nights enough?
For a first taste, yes. You land at 8:59 AM Friday, so you get close to three days. That's enough for the river cruise, Millennium Park, the Art Institute, a deep-dish dinner and a night of blues.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars, and the only adjustment is the clock: Chicago is 1 hour behind Charleston.
Can I cancel the hotel?
Not at Club Quarters Hotel Central Loop, Chicago or Canopy By Hilton Chicago Central Loop. Congress Plaza Hotel Chicago has free cancellation at $750 for the stay, rated 7.1.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License