Chicago from Miami, Oct 16–18: round trip from $430
Chicago from Miami is $430 per person round trip, or $860 for two, for Oct 16–18, 2026 (2 nights). The fare is on Frontier with 1 stop, so it isn't nonstop, and the forecast shows highs of 53–61°F with little rain. The best-value hotel, Holiday Inn Chicago Midway Airport S by IHG, is $495 for the stay.
The flight
$430 per person, round trip
$860 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 | $430 | 1 stop | 19h 34m |
| Frontier | $448 | 1 stop | 32h 18m |
| Frontier | $430 | 1 stop | 28h 10m |
Prices checked Oct 11, 2026, 9:09 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 | $860 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $495 |
| Trip total for two | $1,355 |
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Why go now
At $430 per person, or $860 for two, this round trip is $2 above $428, the median of our earlier checks on this route. That makes it a fair price, not a markdown. It was still the lowest fare we found for this weekend, and the forecast is easy to like for mid-October. Highs run 53–61°F. Saturday has a 4% chance of rain and Sunday 3%, while Friday looks overcast at 36%. That's jacket weather, good for walking around Millennium Park, taking a river cruise and lingering over dinner. There's no deal badge on this one. It's a simple fall city weekend for two, and our sample budget comes to $1,875 for two: flights, the best-value hotel and $520 of spending money. Prices are all-in as of when we checked, and they can change.
The kind of trip this is
This is a city weekend built around food, culture and nightlife: architecture by boat, a big art museum, deep-dish pizza and a late blues set. It suits a couple or a pair of friends who like to walk a lot and eat well. The pace is full but not rushed. Since the outbound flight lands late, plan on one big Saturday and an easy Sunday under clear skies.
Weather in Chicago, Oct 16–18
Highs 53–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 55 °F | 45 °F | 36% |
| Sat, Oct 17 | 53 °F | 42 °F | 4% |
| Sun, Oct 18 | 61 °F | 43 °F | 3% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value at $495 for the stay ($248 a night). It's a 3-star with a 7.5 review score from 226 reviews, and it isn't free to cancel. Heads-up: as the name says, it's by Midway, while this flight lands at O'Hare. Hyatt Centric The Loop Chicago is the top rated, with an 8.5 from 1,005 reviews, at $1,059 for the stay ($530 a night) and free cancellation. Cambria Hotel Chicago Loop - Theatre District, listed as the budget pick, scores 8.1 from 1,258 reviews and costs $855 for the stay ($428 a night), also with free cancellation. Both 4-star options are in The Loop, which puts architecture, theatres and Millennium Park right outside the door.
Holiday Inn Chicago Midway Airport S by IHG
$495 for 2 nights, two guests · $248 a night
See roomsHyatt Centric The Loop Chicago
$1,059 for 2 nights, two guests · $530 a night
See roomsCambria Hotel Chicago Loop - Theatre District
$855 for 2 nights, two guests · $428 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 for the skyline from the water.
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's and pick a side.
- Spend a few hours at the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
- Walk Randolph Street in the West Loop for its restaurant row.
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 | $860 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $495 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,875 |
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 | $430 per person |
| Lowest in the last 30 days | $350 (Oct 12, 2026) |
| Typical price, last 60 days | $428 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars.
- Chicago is 1 hour behind Miami.
- The outbound flight leaves MIA at 5:50 AM Friday and lands at ORD at 12:24 AM Saturday, 19h 34m with 1 stop.
- Bring layers: lows run 42–45°F, and Friday is the one day with a real chance of rain at 36%.
- Hyatt Centric and Cambria have free cancellation. The Holiday Inn doesn't.
Questions readers ask
How much is the flight?
We found $430 per person round trip on Frontier, $860 for two, with taxes and fees included. That's $2 above the $428 median of our earlier checks on this route. Prices change, so check the live fare before you book.
Is it a nonstop?
No. It's 1 stop. The outbound leaves Miami at 5:50 AM Friday, Oct 16 and reaches O'Hare at 12:24 AM Saturday, Oct 17, a total of 19h 34m. The data doesn't show return times.
What is the weather like?
The forecast is cool and mostly dry. Friday is overcast at 55°F with a 36% chance of rain, Saturday is partly cloudy at 53°F, and Sunday is clear at 61°F. Lows run 42–45°F.
Is 2 nights enough?
It's enough for a short getaway. Because of the late arrival, Saturday is your full day: a river cruise, Millennium Park, the Art Institute and blues at night. Sunday has time for deep-dish before heading home.
Do I need a passport?
No. It's a domestic trip in US dollars, and Chicago is just 1 hour behind Miami.
What does the whole weekend cost?
Our sample budget is $1,875 for two: $860 for flights, $495 for the best-value hotel and $520 for spending, which works out to $130 per person per day.
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