Chicago from Buffalo, Oct 16–18: round trip from $413
When we checked, a round trip from Buffalo to Chicago was $413 per person all-in ($826 for two) for Oct 16–18, 2026, which is 2 nights. The fare is on Frontier with one stop, not a nonstop. The forecast shows drizzle on Friday, then mostly clear and clear skies with highs of 52°F and 61°F, and the best-value hotel is $485 for the stay.
The flight
$706 $413 per person, round trip
the highest fare we saw for these dates
$826 for two, taxes and fees included · Frontier · 1 stop · 5h 47m
Out Fri, Oct 16, 1:44 PM – Fri, Oct 16, 6:31 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $413 | 1 stop | 5h 47m |
| United | $575 | nonstop | 2h |
| American | $575 | nonstop | 2h 5m |
Prices checked Oct 12, 2026, 6:50 AM 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 | $826 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $485 |
| Trip total for two | $1,311 |
Regular: $1,897 You pay: $1,311 Saved: $586
the highest fare we saw for these dates.
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Why go now
At $413 per person, or $826 for two, this fare is $293 below the highest fare we saw for these dates. That's 42% less, and it comes from the 12 offers we checked. United and American both had nonstops at $575 per person, so the lower fare means a connection and a 5h 47m trip on the way out. Mid-October falls after the summer beach season and before the holiday markets, so this is a straight city weekend of museums, food and the river. Friday's forecast is 60°F with drizzle. Saturday looks mostly clear at 52°F and Sunday clear at 61°F, with lows of 44°F to 45°F. Bring a jacket and the weekend works for architecture walks and a long deep-dish lunch. These prices are from when we checked and may change.
The kind of trip this is
This is a city getaway built around food, art and architecture. It suits a couple or two friends who like walking all day and eating well. The pace is easy: one big museum, one river cruise and one late night of live blues. Two nights is short, but you land Friday evening and still get a full Saturday plus Sunday to wander.
Weather in Chicago, Oct 16–18
Highs 52–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 60 °F | 45 °F | 48% |
| Sat, Oct 17 | 52 °F | 44 °F | 2% |
| Sun, Oct 18 | 61 °F | 45 °F | 4% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value at $485 for the 2 nights, or $243 a night. It scores 7.5 from 226 reviews, and the price is for a Standard King Room with no meals and no free cancellation. Le Meridien Essex Chicago is the top-rated pick, scoring 8.6 from 380 reviews, at $830 for the stay ($415 a night) with free cancellation. It's in The Loop, which puts architecture, theatres and Millennium Park right outside your door. Sleep Inn Midway Airport is the budget option at $367 ($184 a night). It scores 7.3 from 726 reviews and includes breakfast and free cancellation. One thing to note: two of these hotels are near Midway Airport, but the Frontier flight lands at O'Hare.
Holiday Inn Chicago Midway Airport S by IHG
$485 for 2 nights, two guests · $243 a night
See roomsLe Meridien Essex Chicago
$830 for 2 nights, two guests · $415 a night
See roomsSleep Inn Midway Airport
$367 for 2 nights, two guests · $184 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 Saturday, when the forecast is mostly clear.
- See the Bean and the fountains in Millennium Park, an easy walk from The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's and pick your own winner.
- Spend a few hours at the Art Institute of Chicago, a good indoor plan for cool weather.
- Hear live blues at Kingston Mines for a late 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 Buffalo | Buffalo Niagara International (BUF) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 5h 47m (1 stop) |
| Distance | 451 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $826 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $485 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,831 |
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: Buffalo to Chicago
| Per person | |
|---|---|
| This trip | $413 per person |
| Lowest in the last 30 days | $413 (Oct 12, 2026) |
| Price checks | 4 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- You don't need a passport, you'll pay in US dollars, and Chicago is 1 hour behind Buffalo.
- The outbound Frontier flight leaves BUF at 1:44 PM and lands at ORD at 6:31 PM local time, with one stop.
- Chicago has two airports, O'Hare (ORD) and Midway (MDW). This fare uses O'Hare.
- Le Meridien Essex Chicago and Sleep Inn Midway Airport offer free cancellation, but the Holiday Inn rate doesn't.
- Prices are all-in and come from when we checked. They aren't a promise of what you'll pay later.
Questions readers ask
How much is the flight?
It's $413 per person round trip on Frontier, or $826 for two, with taxes and fees included when we checked. The flight out has one stop and takes 5h 47m.
Is there a nonstop?
Yes. United has a nonstop that leaves at 7:00 AM and lands at 8:00 AM, and American has one at 8:00 AM that lands at 9:05 AM. Both were $575 per person, or $1,150 for two.
What is the weather like?
Friday's forecast is drizzle and 60°F with a 48% chance of rain. Saturday looks mostly clear at 52°F with a 2% chance, and Sunday looks clear at 61°F with a 4% chance. Nights get down to 44°F to 45°F.
Is 2 nights enough?
It's enough for a first visit. You land at 6:31 PM Friday, so you get dinner that night, a full Saturday for the river cruise, the Art Institute and blues, and Sunday for Millennium Park.
What does the whole weekend cost for two?
Our estimate is $1,831 for two: $826 for flights, $485 for the Holiday Inn 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 of 451 miles and you'll use US dollars. Just remember that Chicago runs 1 hour behind Buffalo.
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
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