Chicago from Richmond, Oct 16–18: $1,905 for two, all in
The verdict
Our verdict
Worth it, if
- Nonstop on American, 2h 23m, leaving Richmond at 7:47 AM
- $500 per person, $251 below the typical fare on this route
- La Quinta in the Loop: 8/10 from 3,744 reviews, breakfast included
The catch: Friday shows a 78% chance of drizzle, and a checked bag is about $160 for two, which isn't in the total.
Worth it if you want a weekend of museums, food and blues and don't mind a damp Friday; skip it if you need warm weather.
Worth it if a drizzly Friday won't bother you: $1,905 for two covers the flights at $1,000 plus La Quinta at $905, with taxes and fees included. The trip runs Oct 16–18, 2026, for 2 nights, on a nonstop American flight from Richmond. A checked bag and spending money aren't in that total.
The total, before you go
$1,905 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $1,000 |
| La Quinta Inn & Suites by Wyndham Chicago Downtown, 2 nights, two guests, taxes in | $905 |
| The total, before you go | $1,905 |
| A checked bag each, round trip (not in the total) | about $160 |
$251 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $40 each way per bag on American, $160 for two round trip); 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
$500 per person, round trip
$1,000 for two, taxes and fees included · American · nonstop · 2h 23m
Out Fri, Oct 16, 7:47 AM – Fri, Oct 16, 9:10 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American | $500 | nonstop | 2h 23m |
| United. Operated by Republic Airways DBA United Express | $500 | nonstop | 2h 21m |
| American | $500 | nonstop | 2h 21m |
Prices checked Oct 14, 2026, 3:30 AM EDT. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
The fare is $500 per person, $251 below the typical fare on this route. That's 33% under. We saw 12 offers for these dates, from $500 to $761 per person, and this one is at the low end. In mid-October, Chicago's highs are 58°F on Friday and Saturday and 65°F on Sunday, with lows from 45°F to 49°F. Friday is the wet day, with a 78% chance of drizzle, so plan the Art Institute for then. The chance of rain drops to 7% on Saturday and 0% on Sunday, when the forecast is clear. The 7:47 AM nonstop lands at O'Hare at 9:10 AM local time, so you still get most of Friday. Two nights is short, but with all three hotels in the Loop you won't spend much time getting around. These were the all-in prices when we checked, and they can change.
The kind of trip this is
This is a city weekend built around architecture, museums, deep-dish pizza and live blues. It suits a couple or two friends who like to walk, eat well and stay out a little late. The pace is brisk: two full days split between the Loop and River North, with a nonstop of about two and a half hours at each end and a hotel that serves breakfast.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 58 °F | 48 °F | 78% |
| Sat, Oct 17 | 58 °F | 45 °F | 7% |
| Sun, Oct 18 | 65 °F | 49 °F | 0% |
Where to stay in Chicago
All three hotels are in The Loop, where the architecture, the theatres and Millennium Park are right outside your door. La Quinta Inn & Suites by Wyndham Chicago Downtown is the best-value pick and the one in the total: $905 for the 2 nights ($453 a night), rated 8/10 from 3,744 reviews. You get breakfast, a larger king room with a sofa bed and free cancellation. Hyatt Centric The Loop Chicago is the top-rated choice, scoring 8.5 from 1,003 reviews. It's a 4-star hotel at $1,007 for the stay ($504 a night), room only. Hyatt Place Chicago/Downtown - The Loop, our budget pick, lands in between at $925 ($463 a night), rated 8.2 from 1,959 reviews, room only. All three offer free cancellation. For dinner and drinks, River North is the city's nightlife core, with galleries and steakhouses.
La Quinta Inn & Suites by Wyndham Chicago Downtown
$905 for 2 nights, two guests · $453 a night
See roomsHyatt Centric The Loop Chicago
$1,007 for 2 nights, two guests · $504 a night
See roomsHyatt Place Chicago/Downtown - The Loop
$925 for 2 nights, two guests · $463 a night
See roomsAll hotels in Chicago for these dates
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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 Sunday
- See the Bean and the fountains in Millennium Park, steps from the Loop hotels
- Spend drizzly Friday inside the Art Institute of Chicago
- Eat deep-dish at Lou Malnati's or Pequod's
- 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 | $1,000 |
| Hotel, 2 nights (La Quinta Inn & Suites by Wyndham Chicago Downtown) | $905 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,425 |
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 | $500 per person |
| Lowest in the last 30 days | $490 (Oct 12, 2026) |
| Typical price, last 60 days | $751 |
| Price checks | 9 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars.
- Chicago is 1 hour behind Richmond; the nonstop covers 618 miles in 2h 23m.
- The flight lands at Chicago O'Hare International (ORD); the city also has Chicago Midway International (MDW).
- A checked bag is about $160 for two and isn't included in the $1,905.
- All three hotels list free cancellation; only La Quinta includes breakfast.
Questions readers ask
Is it worth it?
Yes, as long as Friday drizzle doesn't spoil it for you. The fare is $251 per person below the typical fare on this route, the flight is a 2h 23m nonstop, and the hotel in the total scores 8/10 and includes breakfast.
How much is the whole trip for two?
$1,905 all in: $1,000 for two round-trip flights plus $905 for 2 nights at La Quinta, with taxes and fees included. A checked bag, about $160 for two, and spending money are extra.
What is the weather like?
Friday: a high of 58°F with a 78% chance of drizzle. Saturday: overcast with a high of 58°F and a 7% chance of rain. Sunday: clear with a high of 65°F and a 0% chance of rain.
When does the flight leave?
The American nonstop leaves Richmond at 7:47 AM on Friday, Oct 16, and lands at O'Hare at 9:10 AM Chicago time. There are also nonstops at 10:38 AM on United and 11:46 AM on American at the same $500 per person.
Is 2 nights enough?
For a first look, yes. With an early arrival and all three hotels in the Loop, you get Friday for the Art Institute, Saturday for the river cruise and Millennium Park, and a clear Sunday morning before you fly home.
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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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Image credits
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