Chicago from Miami, 16 – 18 Oct: £1,021 for two, all in
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The verdict
Our verdict
Not worth it this week
- Highs 53–61°F, with 4% and 3% rain chances Saturday and Sunday
- Free cancellation at both Loop hotels, rated 8.1 and 8.5
- Fare is $430 per person, $2 above the typical $428
The catch: The Frontier fare has 1 stop and takes 19h 34m, landing at 12:24 AM, and a checked bag is about $240 for two.
Worth it if you can sleep anywhere and only want Saturday and Sunday in the city; skip it if you want a nonstop or a full Friday.
Not worth it this week: the trip for two is $1,355, the Frontier flights at $860 plus Holiday Inn Chicago Midway Airport S by IHG at $495, taxes and fees included, with bags and spending money extra. It's Oct 16–18, 2026, 2 nights, and the flight isn't nonstop: 1 stop and 19h 34m on the way out.
The total, before you go
£1,021 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £648 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £373 |
| The total, before you go | £1,021 |
| Hold luggage each, return (not in the total) | about £181 |
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
£324 per person, return
£648 for two, taxes and fees included · Frontier · 1 stop · 19h 34m
Out Fri, Oct 16, 5:50 AM – Sat, Oct 17, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £324 | 1 stop | 19h 34m |
| Frontier | £338 | 1 stop | 32h 18m |
| Frontier | £324 | 1 stop | 28h 10m |
Prices checked 11 Oct 2026, 21:09 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
Not worth it this week, mostly because of the flight. The fare is $430 per person, $2 above the typical $428 from earlier checks on this route, and the lowest we saw was $350 on Oct 12. The best offer is Frontier with 1 stop: it leaves Miami at 5:50 AM on Friday, Oct 16 and lands at O'Hare at 12:24 AM Saturday, 19h 34m for a trip of 1,192 miles. On a 2-night weekend, that takes a whole day. The weather is the good part: highs of 53–61°F, a 36% rain chance Friday, then 4% Saturday and 3% Sunday, clear by the end. If a shorter routing shows up at a similar fare, the city is ready for a fall weekend of museums, deep-dish and blues.
The kind of trip this is
A fall city weekend: architecture, museums, deep-dish and live blues, at a walking pace in cool weather. It suits a couple or two friends who like long days on foot and late nights out, and who don't mind a jacket in October. With the flight landing after midnight, it's really a Saturday and Sunday trip, so plan a full Saturday and an easy Sunday.
Weather in Chicago, 16 – 18 Oct
Highs 53–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 55 °F | 45 °F | 36% |
| Sat 17 Oct | 53 °F | 42 °F | 4% |
| Sun 18 Oct | 61 °F | 43 °F | 3% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value and the one in the total: $495 for the 2 nights ($248 a night), 7.5 from 226 reviews, but no free cancellation, and it's by Midway rather than downtown, while the flight lands at O'Hare. Cambria Hotel Chicago Loop - Theatre District is the middle pick at $855 for the stay ($428 a night), 8.1 from 1,258 reviews, with free cancellation. Hyatt Centric The Loop Chicago is the top rated at 8.5 from 1,005 reviews, $1,059 for the stay ($530 a night), also with free cancellation. Both put you in The Loop, with architecture, theatres and Millennium Park at your doorstep, and River North is nearby for galleries, steakhouses and nightlife.
Holiday Inn Chicago Midway Airport S by IHG
£373 for 2 nights, two guests · £187 a night
See roomsHyatt Centric The Loop Chicago
£798 for 2 nights, two guests · £399 a night
See roomsCambria Hotel Chicago Loop - Theatre District
£644 for 2 nights, two guests · £323 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 Sunday
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend Friday's cloudier hours inside the Art Institute of Chicago
- 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 Miami | Miami International (MIA), Fort Lauderdale-Hollywood International (FLL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 19h 34m (1 stop) |
| Distance | 1,192 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £648 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £373 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,413 |
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: Miami to Chicago
| Per person | |
|---|---|
| This trip | £324 per person |
| Lowest in the last 30 days | £264 (12 Oct 2026) |
| Typical price, last 60 days | £323 |
| Price checks | 6 |
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; you pay in US dollars.
- Chicago is 1 hour behind Miami.
- The Frontier flight leaves MIA at 5:50 AM, has 1 stop and takes 19h 34m to O'Hare.
- A checked bag is about $240 for two, not in the $1,355 total; resort fees and spending money aren't in it either.
- Prices are all-in as found when we checked and can change; only the two Loop hotels offer free cancellation.
Questions readers ask
Is it worth it?
Not this week for most people. The fare is $430 per person, $2 above the typical $428, and the Frontier routing has 1 stop and takes 19h 34m, landing at 12:24 AM Saturday. The weather and the Loop hotels are good; the flight is the problem.
How much is the whole trip for two?
$1,355, all in: $860 for the flights and $495 for 2 nights at Holiday Inn Chicago Midway Airport S by IHG, taxes and fees included. A checked bag is about $240 for two and isn't in that, nor is spending money or any resort fee.
Do I need a passport?
No. It's a domestic trip from Miami to Chicago, paid in US dollars, and Chicago is 1 hour behind Miami.
What is the weather like?
Highs of 53–61°F with lows of 42–45°F. Friday is overcast with a 36% rain chance, Saturday is partly cloudy at 4% and Sunday is clear at 3%. Pack a jacket.
Is 2 nights enough?
Tight with this flight. Leaving at 5:50 AM Friday and landing at 12:24 AM Saturday leaves Saturday and Sunday for the river cruise, Millennium Park, the Art Institute and deep-dish. A shorter routing would give you Friday back.
Are there other flights?
We saw another Frontier option at $430 per person leaving at 11:15 AM and taking 28h 10m, and one at $448 per person taking 32h 18m. None we found was nonstop.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License