Chicago from Buffalo, 16 – 18 Oct: £988 for two, all in
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The verdict
Our verdict
Worth it, if
- $413 per person, $293 below the highest fare we saw
- Saturday and Sunday clear, with a 2% and 4% rain chance
- Sleep Inn Midway Airport: breakfast and free cancellation, $367 for 2 nights
The catch: Frontier connects, so the outbound takes 5h 47m against 2h nonstops, and a checked bag is about $240 for two, not in the total.
Worth it if you'd rather save on the fare than on the hours; skip it if you want a nonstop or a downtown bed.
Worth it if you can live with a connection: $1,311 for two covers Frontier round-trip flights at $826 plus 2 nights at the Holiday Inn Chicago Midway Airport S by IHG at $485, taxes and fees included. The trip runs Oct 16–18, 2026, Friday to Sunday, and the Frontier flight is not nonstop: 1 stop and 5h 47m on the way out. Checked bags and spending money are not in that total.
The total, before you go
£988 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £623 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £366 |
| The total, before you go | £988 |
| Hold luggage each, return (not in the total) | about £181 |
£221 per person below the highest fare we saw for these dates.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); 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
£311 per person, return
£623 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 | £311 | 1 stop | 5h 47m |
| United | £433 | nonstop | 2h |
| American | £433 | nonstop | 2h 5m |
Prices checked 12 Oct 2026, 06:50 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $413 per person, the Frontier fare is $293 below the highest fare we saw for these dates, a 42% gap, and it's the lowest of the 12 offers we checked. The nonstops on United and American were $575 per person, so the connection is what buys the lower price. The weather lines up well for a two-night stay: Friday brings a 48% chance of drizzle and a high of 60°F, then Saturday is mostly clear at 52°F and Sunday is clear at 61°F, so your two full days are the dry ones. Mid-October falls between the summer lakefront festivals and the holiday markets, which leaves a plain city weekend of architecture, museums, deep-dish and blues. Prices were all-in when we checked and can move before you book.
The kind of trip this is
A city weekend built on walking and eating: river architecture, a world-ranked art museum, deep-dish and a blues club late on Saturday. It suits a couple or two friends who like a full but unhurried pace, and it calls for sweaters, not swimsuits, with lows of 44–45°F. With 2 nights you get one big day, Saturday, plus a Friday evening and a Sunday morning.
Weather in Chicago, 16 – 18 Oct
Highs 52–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 60 °F | 45 °F | 48% |
| Sat 17 Oct | 52 °F | 44 °F | 2% |
| Sun 18 Oct | 61 °F | 45 °F | 4% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value and the hotel in our total: $485 for 2 nights ($243 a night), 7.5 from 226 reviews, room only, no free cancellation. Le Meridien Essex Chicago is the top rated at 8.6 from 380 reviews. It's $830 for the stay ($415 a night) with free cancellation, and it puts you in The Loop, with the architecture, theaters and Millennium Park right outside. Sleep Inn Midway Airport is the budget pick at $367 ($184 a night), 7.3 from 726 reviews, with breakfast and free cancellation. Heads-up: both Midway hotels are by the airport, not downtown, and your flight lands at O'Hare (ORD).
Holiday Inn Chicago Midway Airport S by IHG
£366 for 2 nights, two guests · £183 a night
See roomsLe Meridien Essex Chicago
£626 for 2 nights, two guests · £313 a night
See roomsSleep Inn Midway Airport
£277 for 2 nights, two guests · £139 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 clear Saturday
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago if Friday's drizzle shows up
- Hear live blues at Kingston Mines on Saturday night
Also worth it
- 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 | £623 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £366 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,380 |
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 | £311 per person |
| Lowest in the last 30 days | £311 (12 Oct 2026) |
| Price checks | 4 |
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).
- No passport needed, and you pay in US dollars
- Chicago is 1 hour behind Buffalo
- The outbound leaves Buffalo at 1:44 PM and lands at O'Hare at 6:31 PM local time, with 1 stop
- We estimate spending money at $520 for two for the 2 days, which brings the trip to $1,831
- Only Le Meridien Essex Chicago and Sleep Inn Midway Airport offer free cancellation
Questions readers ask
Is it worth it?
Yes, if a connection doesn't bother you. The fare is $413 per person, $293 below the highest fare we saw for these dates, and the weekend looks mostly dry. If you want a nonstop, United and American had them at $575 per person.
How much is the whole trip for two?
$1,311 for two, all in: $826 for the Frontier flights plus $485 for 2 nights at the Holiday Inn Chicago Midway Airport S by IHG, taxes and fees included. A checked bag is about $240 for two and isn't included, and neither is spending money.
Is the flight nonstop?
No. Frontier connects once, and the outbound takes 5h 47m, leaving at 1:44 PM and landing at O'Hare at 6:31 PM local time. The nonstops we found take 2h to 2h 5m.
What is the weather like?
Friday has a 48% chance of drizzle with a high of 60°F. Saturday is mostly clear at 52°F, and Sunday is clear at 61°F. Lows sit at 44–45°F, so bring a warm layer.
Is 2 nights enough?
For a first taste, yes. You get Friday evening, a full Saturday for the river cruise, Millennium Park and blues, and Sunday morning for the Art Institute or deep-dish before you fly home.
Do I need a passport?
No. It's a domestic trip, and you'll pay in US dollars.
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All trips from Buffalo · 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 15 Oct 2026.
Image credits
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