Chicago from Philadelphia, Oct 23–25: round trip from $314
When we checked, nonstop round trips from Philadelphia to Chicago on Frontier cost $314 per person, or $628 for two, for Friday to Sunday, Oct 23–25, 2026 (2 nights). The forecast shows highs of 55–71°F and a small chance of rain. Our best-value hotel, Hilton Chicago in The Loop, is $522 for the stay.
The flight
$333 $314 per person, round trip
the typical fare on this route
$628 for two, taxes and fees included · Frontier · nonstop · 2h 30m
Out Fri, Oct 23, 9:09 PM – Fri, Oct 23, 10:39 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $314 | nonstop | 2h 30m |
| Frontier | $357 | 1 stop | 9h 19m |
| Frontier | $362 | 1 stop | 13h 7m |
Prices checked Oct 12, 2026, 10:54 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 | $628 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,150 |
Regular: $1,188 You pay: $1,150 Saved: $38
the typical fare on this route.
Tweak this trip
Why go now
At $314 per person round trip, or $628 for two, this fare is $19 below the typical fare on this route. Our earlier checks put that typical fare at $333, so you're 6% under. We saw 12 offers ranging from $314 to $483, and the cheapest one is also the nonstop. A heads-up: the low over the last 30 days was $284, so this isn't the floor. It's a fair price for a Friday-to-Sunday trip, though. The flight leaves Philadelphia at 9:09 PM on Friday, Oct 23 and lands at O'Hare at 10:39 PM Chicago time, which means you can leave after work. Friday's high is 71°F, dropping to 55°F by Sunday, with a 23% to 31% chance of rain each day. Pack a jacket. It's good weather for museums, a river cruise and long dinners.
The kind of trip this is
This is a city weekend built around food, architecture and art. It suits couples or a pair of friends who want two full days of walking, eating and looking up at buildings. You land late Friday, so the real trip is a busy Saturday of museums and a river cruise followed by an evening of blues. Sunday is slower, with a park stroll and one more deep-dish before you fly home.
Weather in Chicago, Oct 23–25
Highs 55–71°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 71 °F | 57 °F | 23% |
| Sat, Oct 24 | 60 °F | 53 °F | 23% |
| Sun, Oct 25 | 55 °F | 48 °F | 31% |
Where to stay in Chicago
Hilton Chicago is our best value at $522 for the 2 nights, or $261 a night, for a King Room. It's a 3-star with a 7.9 review score from 981 reviews, but heads-up: there's no free cancellation. It's in The Loop, which puts architecture, theatres and Millennium Park right outside. If you want the top-rated stay, Eurostars Magnificent Mile is $773 for the stay ($387 a night). It's a 4-star in River North with an 8.7 score from 2,285 reviews and free cancellation, and the area is the city's nightlife core with galleries and steakhouses nearby. Congress Plaza Hotel Chicago is our budget pick at $550 ($275 a night) for a Queen Room. It's also a 4-star in The Loop, scores 7.1 from 4,548 reviews and has free cancellation. All three are room only.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsEurostars Magnificent Mile
$773 for 2 nights, two guests · $387 a night
See roomsCongress Plaza Hotel Chicago
$550 for 2 nights, two guests · $275 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 to see the skyline from the water.
- 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 and settle the debate yourselves.
- Spend a few hours at the Art Institute of Chicago, a good plan for an overcast day.
- 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 Philadelphia | Philadelphia International (PHL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 30m nonstop |
| Distance | 663 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $628 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,670 |
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: Philadelphia to Chicago
| Per person | |
|---|---|
| This trip | $314 per person |
| Lowest in the last 30 days | $284 (Oct 12, 2026) |
| Typical price, last 60 days | $333 |
| Price checks | 10 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- It's a domestic trip, so no passport is needed and you'll pay in US dollars.
- Chicago is 1 hour behind Philadelphia, and the nonstop takes 2h 30m to cover 663 miles.
- The flight lands at Chicago O'Hare International (ORD). Chicago Midway International (MDW) also serves the city.
- Prices are all-in, taxes and fees included, as found when we checked. They can change.
- All three hotels are room only. Hilton Chicago has no free cancellation; the other two do.
Questions readers ask
How much is the flight?
It's $314 per person round trip on Frontier, nonstop, or $628 for two, all-in when we checked. That's $19 below the typical fare on this route. Fares we saw ranged from $314 to $483.
What time does the flight leave?
It leaves Philadelphia at 9:09 PM on Friday, Oct 23 and lands at O'Hare at 10:39 PM Chicago time. The flight takes 2h 30m, and Chicago is 1 hour behind.
What is the weather like?
Friday has a high of 71°F with drizzle. Saturday and Sunday are overcast, with highs of 60°F and 55°F and lows down to 48°F. The chance of rain each day is 23% to 31%.
What does the whole weekend cost for two?
Our estimate comes to $1,670 for two people: $628 for flights, $522 for Hilton Chicago and $520 for spending money, which works out to $130 per person per day.
Do I need a passport?
No. It's a domestic trip within the US, and you'll pay in US dollars.
Is 2 nights enough?
It's enough for the highlights if you plan around a late Friday arrival. Saturday covers the river cruise, the Art Institute and an evening of blues, and Sunday leaves time for Millennium Park and deep-dish.
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License