Chicago from Miami, Oct 30–Nov 1: $340 per person, round trip
The verdict
Our verdict
Worth it, if
- $340 per person, $88 (21%) below the typical fare
- Leave Friday 11:39 AM, land in Chicago 7:59 PM
- River cruise, Art Institute and deep-dish fill a 2-night city weekend
The catch: There's one stop and 9h 20m of travel on the way out, and a checked bag is about $240 for two on top of the fare.
Worth it if you pack light and want a cool-weather city weekend of museums and food; skip it if a 9h 20m one-stop flight ruins it for you.
Worth it if you can live with one stop: Frontier has it at $340 per person round trip, or $680 for two, with taxes and fees included when we checked on Oct 16, 2026. It's Oct 30–Nov 1, 2026, 2 nights over a weekend. It isn't nonstop: there's one stop, and the trip out takes 9h 20m.
The total, before you go
$680 for two · 2 nights · flights, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $680 |
| The total, before you go | $680 |
| A checked bag each, round trip (not in the total) | about $240 |
$88 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip). Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$340 per person, round trip
$680 for two, taxes and fees included · Frontier · 1 stop · 9h 20m
Out Fri, Oct 30, 11:39 AM – Fri, Oct 30, 7:59 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $340 | 1 stop | 9h 20m |
| Frontier | $381 | 1 stop | 24h 50m |
| Frontier | $393 | 1 stop | 28h 35m |
Prices checked Oct 16, 2026, 12:16 AM EDT. Prices change; the binding price is the one on the booking site.
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
Tweak this trip
Why now
At $340 per person, the fare is $88 below the typical fare on this route, a 21% gap. It's also the lowest in 30 days across the 18 checks we've run. The 12 offers we saw ranged from $340 to $449 per person, so this one is at the bottom of that range. For two, the flights come to $680 with taxes and fees included, as found on Oct 16, 2026. Prices move, so it may not hold. The dates fall on a cool late-fall weekend: typical highs of 51–56°F and lows near 41°F, overcast skies and drizzle on Sunday. That's weather for museums, a river cruise in a jacket and long dinners, not the lakefront beaches. You don't need a passport and the clock only moves 1 hour, so it works as a quick city break that doesn't take much planning.
The kind of trip this is
This is a compact city weekend built around architecture, art and food. Picture a river cruise past the skyscrapers, an afternoon at the Art Institute, deep-dish for dinner and live blues late at night. It suits a couple or two friends who like to walk, eat well and stay out a little. The pace is steady, and there are indoor backups for gray, cool days.
Weather in Chicago, Oct 30–Nov 1
Typical highs 51–56°F, lows near 41°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Fri, Oct 30 | 56 °F | 46 °F | Overcast |
| Sat, Oct 31 | 54 °F | 40 °F | Overcast |
| Sun, Nov 1 | 51 °F | 37 °F | Drizzle |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Chicago
We didn't find hotel prices for these dates, so the price above covers flights only and the hotel is extra. With just 2 nights, where you stay matters more than usual. The Loop puts architecture, theatres and Millennium Park at your doorstep, which is handy for the river cruise and the Art Institute. River North is the city's nightlife core, with galleries and steakhouses, so it suits a plan that runs late. West Loop has converted warehouses and the restaurant row on Randolph Street, a good base for a food weekend. Magnificent Mile / Streeterville means shopping on Michigan Avenue and lakefront hotels. Before you book on the hotel's site, check the cancellation terms and any nightly fees.
All hotels in Chicago for these dates
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, and bring a warm layer for highs of 51–56°F
- See the Bean in Millennium Park, steps from The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend a gray afternoon at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Friday or Saturday night
Also worth it
- See the Bean and the fountains in Millennium Park
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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
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 | 9h 20m (1 stop) |
| Distance | 1,192 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $680 |
| Hotel, 2 nights | $0 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,200 |
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 | $340 per person |
| Lowest in the last 30 days | $340 (Oct 16, 2026) |
| Typical price, last 60 days | $428 |
| Price checks | 18 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- You don't need a passport, and you pay in US dollars.
- Chicago is 1 hour behind Miami.
- The outbound leaves MIA at 11:39 AM and lands at Chicago O'Hare (ORD) at 7:59 PM, with one stop, 9h 20m in all.
- The fare includes taxes and fees; a checked bag is about $240 for two on top of it.
- Other airports to check: Fort Lauderdale-Hollywood (FLL) on the Miami side and Chicago Midway (MDW) on the Chicago side.
Questions readers ask
Is it worth it?
Worth it if you can handle one stop and 9h 20m on the way out. The fare is $340 per person, $88 below the typical fare on this route, and the lowest in 30 days of our checks.
How much is the whole trip for two?
Flights are $680 for two with taxes and fees included, as found on Oct 16, 2026. We didn't find a hotel price for these dates, so add the hotel yourself, plus about $240 for two if you check bags.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars, and Chicago is just 1 hour behind Miami.
What is the weather like?
Typical highs are 51–56°F with lows near 41°F. Friday and Saturday look overcast and Sunday shows drizzle, so pack a warm layer and a rain jacket.
Is 2 nights enough?
For a focused city weekend, yes. You land Friday at 7:59 PM, which leaves the evening for blues or deep-dish and Saturday for the river cruise and the Art Institute. Our check didn't include return flight times, so look at those before you book.
Is there a nonstop?
Not at this price. The fare we found is on Frontier with one stop. The other offers we saw were also one-stop Frontier flights, at $381 and $393 per person, and they took much longer.
Also found for you
The newest finds from Miami.
Just found · from MiamiLowest in 30 daysWorth it, if
Nashville
Oct 30–Nov 1, 2026 · 2 nights
- $221 per person below the typical fare on this route
- Lowest in 30 days on this route
- Holiday Inn Nashville Airport by IHG, rated 8.1 by 333 guests
$903 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $604 + hotel $262 + resort fee $37, taxes in · a checked bag each adds about $240
Frontier · with a stop · 9h 26m
The catch: Not nonstop: a stop on the way, 9h 26m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Tweak this trip
Just found · from MiamiWorth it, if
Chicago
Oct 23–25, 2026 · 2 nights
- Highs of 64–71°F with a 9–17% chance of rain
- Hilton Chicago in The Loop, rated 7.9 from 982 reviews
- $430 per person, right at the typical fare for this route
$1,569 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $860 + hotel $612 + resort fee $97, taxes in · a checked bag each adds about $240
Frontier · with a stop · 19h 34m
The catch: The flight out has one stop and takes 19h 34m, landing at 12:24 AM Saturday, and a checked bag is about $240 for two.
Worth it if you want one full city day of food, art and blues; skip it if a 19h 34m flight out would eat your weekend.
Tweak this trip
Just found · from MiamiWorth it, if
Atlanta
Nov 27–30, 2026 · 3 nights
- Frontier nonstop, 2h 19m, leaving MIA at 8:08 AM
- $148 per person, $109 below the highest fare we saw
- Hilton Atlanta in Downtown, review score 8 from 2,873 reviews
$713 for two · 3 nights · flights, hotel, taxes, fees & the resort fee
Flights $296 + hotel $353 + resort fee $64, taxes in · a checked bag each adds about $240
Frontier · nonstop · 2h 19m
The catch: The Frontier fare doesn't include a checked bag, which runs about $240 for two, and the Hilton Atlanta rate has no free cancellation.
Worth it if you pack light and want a jacket-weather city weekend of history and food; skip it if you need warm weather or flexible cancellation.
Tweak this trip
More trips
Next weekend · from MiamiWorth it, if
Orlando
Oct 23–25, 2026 · 2 nights
- EPCOT Food & Wine Festival and Halloween events are on in October
- $241 per person all-in, the typical fare for this route
- Highs of 73–80°F with rain chances from 10% to 24%
$241 per person · round trip · taxes & fees
Frontier · with a stop · 9h 13m
The catch: The Frontier fare has one stop and takes 9h 13m overnight to cover 200 miles, and a checked bag is about $240 for two.
Worth it if you can sleep on a red-eye and want one big park day; skip it if you'd rather drive or need a relaxed pace.
Just found · from Miami28% below typicalWorth it, if
Aruba
Nov 14–21, 2026 · 7 nights
- $453 per person, $219 below the typical fare on this route
- Tuscany Residence Aruba on Eagle Beach: 9.5 from 123 reviews
- Free cancellation at all three hotels, highs of 85–86°F all week
$3,528 for two · 7 nights · flights, hotel, taxes & fees
Flights $950 + hotel $2,578, taxes in · a checked bag each adds about $160
Avianca · with a stop · 8h 5m
The catch: The $453 COPA fare has one stop and takes 15h 29m; a checked bag is about $160 for two, and any resort fee isn't in the total.
Worth it if you want a warm, easygoing beach week and don't mind a long flight day; skip it if drizzle would spoil your vacation.
Just found · from MiamiLowest in 30 daysWorth it, if
Nashville
Oct 30–Nov 1, 2026 · 2 nights
- $221 per person below the typical fare on this route
- Lowest in 30 days on this route
- Holiday Inn Nashville Airport by IHG, rated 8.1 by 333 guests
$903 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $604 + hotel $262 + resort fee $37, taxes in · a checked bag each adds about $240
Frontier · with a stop · 9h 26m
The catch: Not nonstop: a stop on the way, 9h 26m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from MiamiWorth it, if
Atlanta
Nov 27–30, 2026 · 3 nights
- Frontier nonstop, 2h 19m, leaving MIA at 8:08 AM
- $148 per person, $109 below the highest fare we saw
- Hilton Atlanta in Downtown, review score 8 from 2,873 reviews
$713 for two · 3 nights · flights, hotel, taxes, fees & the resort fee
Flights $296 + hotel $353 + resort fee $64, taxes in · a checked bag each adds about $240
Frontier · nonstop · 2h 19m
The catch: The Frontier fare doesn't include a checked bag, which runs about $240 for two, and the Hilton Atlanta rate has no free cancellation.
Worth it if you pack light and want a jacket-weather city weekend of history and food; skip it if you need warm weather or flexible cancellation.
Read next: Cheapest weeks to fly: school breaks vs the week after · Balcony or inside cabin: cruisers say worth it, about 2 to 1
All trips from Miami · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.