Chicago from Richmond, 23 – 25 Oct: £1,262 for two, all in
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The verdict
Our verdict
Worth it, because
- Nonstop on American, 2h 23m, leaving Richmond at 7:47 AM
- $490 per person, $248 below the typical fare on this route
- Highs of 68–72°F with a 5% rain chance Friday and Saturday
The catch: A checked bag is about $160 for two and isn't in the total, and you can't cancel the Aloft room for free.
Worth it if you want a walkable city weekend of food, art and live blues; skip it if you need a refundable room at the Aloft.
Worth it for the two of you: $1,672 for two, all in. That's the flights at $980 plus 2 nights at Aloft by Marriott Chicago Mag Mile at $597 and its $95 property fee, with taxes and fees included, but not checked bags or spending money. You fly Friday to Sunday, Oct 23–25, 2026, nonstop on American from Richmond in 2h 23m.
The total, before you go
£1,262 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £740 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | £451 |
| Resort fee, collected at the desk | £72 |
| The total, before you go | £1,262 |
| Hold luggage each, return (not in the total) | about £121 |
£187 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on American, £121 for two return); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£370 per person, return
£740 for two, taxes and fees included · American · nonstop · 2h 23m
Out Fri, Oct 23, 7:47 AM – Fri, Oct 23, 9:10 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American | £370 | nonstop | 2h 23m |
| United. Operated by Gojet Airlines DBA United Express | £370 | nonstop | 2h 24m |
| American | £370 | nonstop | 2h 21m |
Prices checked 16 Oct 2026, 00:39 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
The fare is $490 per person, $248 below the typical fare on this route, which works out to $738 per person across the 17 checks we ran. That's 34% under, and it's the lowest fare we've seen in 30 days. For two, the flights come to $980 instead of $1,476. The forecast looks good for late October: highs of 72°F on Friday, 69°F on Saturday and 68°F on Sunday, overcast, with a 5% to 12% chance of rain. That's good walking weather for the river, the lakefront and Millennium Park. The 7:47 AM nonstop lands at O'Hare at 9:10 AM local time, so you get most of Friday in the city. You don't need a passport or a currency exchange, and the time change is just one hour. These prices were all-in when we checked, and they can change before you book.
The kind of trip this is
A city weekend built on food, architecture and music. It suits a couple or two friends who like to walk all day, eat well and stay out late for a live blues set. The pace is full but easy: two nights moving between The Loop, River North and West Loop, with deep-dish, a river cruise and a big museum on the list, and no jet lag to recover from.
Weather in Chicago, 23 – 25 Oct
Highs 68–72°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 72 °F | 59 °F | 5% |
| Sat 24 Oct | 69 °F | 58 °F | 5% |
| Sun 25 Oct | 68 °F | 58 °F | 12% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile is our best-value pick and the hotel in the total: $597 for the 2 nights ($299 a night) in a Superior King Room. It scores 8.1 from 2,536 reviews, and the total already counts its $95 fee paid at the property. It's in Streeterville, part of Magnificent Mile / Streeterville, for Michigan Avenue shopping and the lakefront. Hampton Inn Chicago West Loop Fulton Market Area is the top-rated pick at 8.8 from 776 reviews. It's $630 for the stay with breakfast, plus a $100 property fee, and the West Loop puts you near the restaurant row on Randolph Street. Congress Plaza Hotel Chicago is the budget pick at $563 ($282 a night), with a score of 7.1 from 4,525 reviews. It's in The Loop and charges an $89 property fee, and it's the only one of the three with free cancellation.
Aloft by Marriott Chicago Mag Mile
£451 for 2 nights, two guests · £226 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£476 for 2 nights, two guests · £238 a night
See roomsCongress Plaza Hotel Chicago
£425 for 2 nights, two guests · £213 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 to see the skyline from the water
- See the Bean and the fountains in Millennium Park in The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend an afternoon at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Richmond | Richmond International (RIC) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 23m nonstop |
| Distance | 618 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £740 |
| Hotel, 2 nights (Aloft by Marriott Chicago Mag Mile) | £451 |
| Food, getting around and tickets, 2 days for two | £393 |
| Total for two | £1,583 |
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: Richmond to Chicago
| Per person | |
|---|---|
| This trip | £370 per person |
| Lowest in the last 30 days | £370 (16 Oct 2026) |
| Typical price, last 60 days | £557 |
| Price checks | 17 |
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).
- You don't need a passport: it's a domestic trip and you pay in US dollars.
- Chicago is 1 hour behind Richmond, and the 618-mile nonstop takes 2h 23m.
- Chicago has two airports, O'Hare (ORD) and Midway (MDW); this fare flies into O'Hare.
- The total doesn't include checked bags, about $160 for two, or spending money, which we put at $520 for two.
- Of the three hotels, only Congress Plaza Hotel Chicago offers free cancellation.
Questions readers ask
Is it worth it?
Yes, for the two of you. The nonstop fare is $490 per person, 34% under the typical $738. The forecast shows highs of 68–72°F with little rain, and you don't need a passport. The catch: checked bags cost about $160 for two, and the Aloft room isn't refundable.
How much is the whole trip for two?
$1,672, all in: $980 for the flights plus $597 for 2 nights at Aloft by Marriott Chicago Mag Mile and its $95 property fee, with taxes and fees included. On top of that, add about $160 if you each check a bag, and the $520 we set aside for two people's spending.
What are the flight times?
The American nonstop leaves Richmond at 7:47 AM on Friday, Oct 23 and lands at O'Hare at 9:10 AM local time. Other nonstops at $490 per person leave at 11:46 AM on American and 1:00 PM on United.
What is the weather like?
Overcast and mild. The forecast shows a high of 72°F and a low of 59°F on Friday, then 69°F and 58°F on Saturday, then 68°F and 58°F on Sunday. The rain chance is 5% on Friday and Saturday and 12% on Sunday.
Is 2 nights enough?
For a first visit, yes. The 9:10 AM arrival gives you most of Friday, plus all of Saturday and part of Sunday, depending on your return flight. That's enough time for the river cruise, Millennium Park, the Art Institute, a deep-dish dinner and a night of blues.
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All trips from Richmond · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Prices converted from US dollars at the rate of 16 Oct 2026.
Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License