Chicago from Pittsburgh, Oct 16–18: $1,648 for two, all in
The verdict
Our verdict
Worth it, if
- $418 per person, $241 below the typical fare on this route
- La Quinta in The Loop: 8 from 3,744 reviews, breakfast included
- Free cancellation at La Quinta, and Sunday's forecast is clear at 65°F
The catch: The Frontier fare has one stop and takes 13 hours overnight, landing at 7:51 AM Saturday, so you'll spend Friday's hotel night in transit.
Worth it if you'll trade a night of sleep for the lower fare; skip it if you want a nonstop and a full Friday evening in Chicago.
Worth it if you can handle an overnight connection: $1,648 for two, all in, covers the Frontier flights at $836 plus La Quinta Inn & Suites by Wyndham Chicago Downtown at $812, with taxes and fees included. The trip runs Oct 16–18, 2026, for 2 nights. The Frontier fare isn't nonstop: it has one stop, takes 13 hours and leaves at 7:51 PM on Friday.
The total, before you go
$1,648 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $836 |
| La Quinta Inn & Suites by Wyndham Chicago Downtown, 2 nights, two guests, taxes in | $812 |
| The total, before you go | $1,648 |
| A checked bag each, round trip (not in the total) | about $240 |
$241 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 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
$418 per person, round trip
$836 for two, taxes and fees included · Frontier · 1 stop · 13h
Out Fri, Oct 16, 7:51 PM – Sat, Oct 17, 7:51 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $418 | 1 stop | 13h |
| United. Operated by Republic Airways DBA United Express | $597 | nonstop | 1h 48m |
| United | $597 | nonstop | 1h 43m |
Prices checked Oct 14, 2026, 10:44 AM EDT. Prices change; the binding price is the one on the booking site.
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Why now
The fare is the reason: $418 per person, $241 below the typical fare on this route. That typical fare is $659, so this one is 37% lower, and it's the lowest in 30 days. Across the 12 offers we checked, fares ran from $418 to $803. For two, that's $836 in flights plus $812 for the hotel, or $1,648 all in. A checked bag, any resort fee and spending money aren't in that total. Mid-October in Chicago calls for a jacket. Friday has an 82% chance of rain, Saturday is overcast at 58°F and Sunday is clear at 65°F with a 0% chance of rain. Because you land Saturday morning, you miss Friday's rain and get the two drier days for the river cruise and Millennium Park. These prices are what we found 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, all close to a hotel in The Loop. The pace is full but short. Saturday and Sunday do most of the work, since you land early Saturday. It suits couples or friends who like to walk a city, eat well and stay out for music. If you're after rest or a beach, this isn't that trip.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 59 °F | 49 °F | 82% |
| Sat, Oct 17 | 58 °F | 46 °F | 12% |
| Sun, Oct 18 | 65 °F | 50 °F | 0% |
Where to stay in Chicago
All three picks are in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. La Quinta Inn & Suites by Wyndham Chicago Downtown is the best value and the hotel in our total. It's $812 for 2 nights, or $406 a night, rated 8 from 3,744 reviews, with breakfast and free cancellation in a larger king room with a sofa bed. Le Meridien Essex Chicago is the top-rated pick at 8.6 from 378 reviews. It's a 4-star at $984 for the stay, room only, with no free cancellation. Club Quarters Hotel Central Loop, Chicago is a 4-star rated 8.2 from 5,335 reviews, at $893 for the stay, room only and also without free cancellation. For a night out, River North is the city's nightlife core.
La Quinta Inn & Suites by Wyndham Chicago Downtown
$812 for 2 nights, two guests · $406 a night
See roomsLe Meridien Essex Chicago
$984 for 2 nights, two guests · $492 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 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 dry, clear Sunday
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend overcast Saturday inside the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Pittsburgh | Pittsburgh International (PIT) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 13h (1 stop) |
| Distance | 409 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $836 |
| Hotel, 2 nights (La Quinta Inn & Suites by Wyndham Chicago Downtown) | $812 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,168 |
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: Pittsburgh to Chicago
| Per person | |
|---|---|
| This trip | $418 per person |
| Lowest in the last 30 days | $418 (Oct 14, 2026) |
| Typical price, last 60 days | $659 |
| Price checks | 6 |
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 one hour behind Pittsburgh.
- The Frontier fare flies Pittsburgh International (PIT) to Chicago O'Hare (ORD) with one stop and takes 13 hours for 409 miles.
- A checked bag is about $240 for two and isn't in the $1,648 total.
- Only La Quinta offers free cancellation; the other two hotels don't.
Questions readers ask
Is it worth it?
Worth it if the overnight connection doesn't bother you. The fare is $418 per person, 37% below the typical $659 on this route. The hotel in the total has breakfast, free cancellation and a score of 8 from 3,744 reviews.
How much is the whole trip for two?
It's $1,648 all in, with taxes and fees included: $836 for the Frontier flights and $812 for 2 nights at La Quinta. A checked bag at about $240 for two, any resort fee and spending money are extra.
Is there a nonstop?
Yes. United has nonstops from PIT to ORD that take 1h 43m to 1h 48m, at $597 per person, or $1,194 for two in flights. That's $179 more per person than the Frontier fare.
What's the weather like?
Friday shows rain with an 82% chance, but you'll be in transit. Saturday is overcast with a high of 58°F and a 12% chance of rain. Sunday is clear at 65°F with a 0% chance.
Is 2 nights enough?
With the Frontier fare, you land at 7:51 AM Saturday. That gives you one full day plus Sunday, which is enough time for the river cruise, the Art Institute, deep-dish and a blues club.
Do I need a passport?
No. It's a domestic trip, you'll pay in US dollars and Chicago is just one hour behind Pittsburgh.
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