Chicago from Orlando, 23 – 25 Oct: £912 for two, all in
The verdict
Our verdict
Worth it, because
- Nonstop on Frontier, 3h 11m
- £24 per person below the typical fare on this route
- Lowest in 30 days on this route
The catch: Seat selection on basic fares and hold luggage (about £181 for two, return) are extra; everything else is in the total.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Chicago is 2 nights from Orlando, 23 – 25 Oct 2026. The cheapest round trip we found is £195 per person (Frontier, nonstop, 3h 11m), 11% below the typical £219 on this route. Hotels start at £213 a night; Highs 68–72°F, little rain expected.
The total, before you go
£912 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £390 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | £451 |
| Resort fee, collected at the desk | £72 |
| The total, before you go | £912 |
| Hold luggage each, return (not in the total) | about £181 |
£24 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£195 per person, return
£390 for two, taxes and fees included · Frontier · nonstop · 3h 11m
Out Fri, Oct 23, 5:20 AM – Fri, Oct 23, 7:31 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £195 | nonstop | 3h 11m |
| Frontier | £258 | 1 stop | 8h |
| Frontier | £195 | nonstop | 3h 18m |
Prices checked 15 Oct 2026, 22:59 GMT-4. 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
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Why Chicago
Why we picked it: Chicago is the best value we priced for the weekend: $258 round trip, nonstop, 11% under the typical price.
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Weather in Chicago, 23 – 25 Oct
Highs 68–72°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 72 °F | 59 °F | 5% |
| Sat 24 Oct | 69 °F | 58 °F | 5% |
| Sun 25 Oct | 68 °F | 58 °F | 12% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile
£451 for 2 nights, two guests · £226 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£476 for 2 nights, two guests · £238 a night
See roomsCongress Plaza Hotel Chicago
£425 for 2 nights, two guests · £213 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
Signature experiences
- Take the Chicago Architecture Foundation river cruise
- 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
- Catch a Cubs game at Wrigley Field
- Hear live blues at Kingston Mines
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Getting there and around
| Airports in Orlando | Orlando International (MCO), Orlando Sanford International (SFB) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 3h 11m nonstop |
| Distance | 986 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £390 |
| Hotel, 2 nights (Aloft by Marriott Chicago Mag Mile) | £451 |
| Food, getting around and tickets, 2 days for two | £393 |
| Total for two | £1,233 |
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: Orlando to Chicago
| Per person | |
|---|---|
| This trip | £195 per person |
| Lowest in the last 30 days | £195 (16 Oct 2026) |
| Typical price, last 60 days | £219 |
| Price checks | 9 |
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).
Questions readers ask
How much does 2 nights in Chicago from Orlando cost?
About £1,233 for two: £390 in flights, £451 for the hotel and £393 for food, getting around and tickets.
What is the weather like in Chicago 23 – 25 Oct?
Highs 68–72°F, little rain expected
Do I need a passport for Chicago?
No. No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
How long is the flight from Orlando to Chicago?
3h 11m nonstop on Frontier, on the fare we found.
Is £195 a good price for Orlando to Chicago?
It is 11% below the typical £219 per person we see on this route, which is why it made the list.
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All trips from Orlando · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Prices converted from US dollars at the rate of 16 Oct 2026.
Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License