Orlando from Chicago, 14 – 21 Nov: £996 for two, all in
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The verdict
Our verdict
Worth it, if
- £22 per person below the typical fare on this route
- B&B HOTEL Orlando International Drive near Universal - Newly Renovated!, rated 8.8 by 1,365 guests
- Typical highs 74–78°F, lows near 60°F this time of year
The catch: Not nonstop: a stop on the way, 11h in all.
Worth it with kids who are up for long days; skip it if you want quiet.
Round-trip flights from Chicago to Orlando were $265 per person ($529 for two) for Nov 14–21, 2026, 7 nights, on F9 with one stop when we checked. Expect highs of 74–78°F and lows near 60°F. The best-value hotel is $113 a night, or $793 for the stay.
The total, before you go
£996 for two · 7 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £399 |
| B&B HOTEL Orlando International Drive near Universal - Newly Renovated!, 7 nights, two guests, taxes in | £598 |
| The total, before you go | £996 |
| Hold luggage each, return (not in the total) | about £181 |
£22 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); 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
£200 per person, return
£399 for two, taxes and fees included · Frontier · 1 stop · 11h
Out Sat, Nov 14, 9:51 AM – Sat, Nov 14, 1:47 PM · back Sat, Nov 21, 6:40 AM – Sat, Nov 21, 1:44 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £200 | 1 stop | 11h |
| Frontier | £218 | nonstop | 6h 1m |
| Frontier | £203 | 1 stop | 16h 13m |
Prices checked 13 Oct 2026, 20:40 GMT-5. 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 $265 per person round trip, this fare is $29 below the typical fare on this route, 10% under the $294 median of our 15 earlier checks. We saw 12 offers, and fares ran from $265 to $293, so this one sits at the bottom of that range. Prices are all-in as found and can change, so check the live fare before you book. Mid-November is a mild window, with typical highs of 74–78°F and lows near 60°F. That's comfortable for long park days, without the hot, stormy summer afternoons. Seven nights leaves room for Magic Kingdom, EPCOT, Universal and Epic Universe, with slower days in between. Our sample budget for two comes to $3,143: $530 for flights, $793 for the best-value hotel and $1,820 for spending.
The kind of trip this is
This is a theme-park week with a side of shopping and a night out or two. It suits couples or friends who want to fill their days with rides, fireworks and food, then come back to a pool. The pace is up to you: full park days back to back, or a park day followed by an easy day on International Drive or out on the river.
Weather in Orlando, 14 – 21 Nov
Typical highs 74–78°F, lows near 60°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Sat 14 Nov | 78 °F | 62 °F | Drizzle |
| Sun 15 Nov | 77 °F | 62 °F | Clear |
| Mon 16 Nov | 77 °F | 60 °F | Partly cloudy |
| Tue 17 Nov | 74 °F | 60 °F | Overcast |
| Wed 18 Nov | 74 °F | 58 °F | Overcast |
| Thu 19 Nov | 77 °F | 59 °F | Overcast |
| Fri 20 Nov | 75 °F | 60 °F | Overcast |
| Sat 21 Nov | 77 °F | 59 °F | Overcast |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Orlando
We found three options, all room only, with prices for the full 7-night stay when we checked. B&B HOTEL Orlando International Drive near Universal - Newly Renovated is the best value at $793 total, or $113 a night. It scores 8.8 from 1,365 reviews and the room has two queen beds and a pool view, but there's no free cancellation. Sheraton Vistana Villages Resort Villas, I-Drive Orlando is the top rated, with an 8.9 from 1,830 reviews. It's $1,409, or $201 a night, for a one-bedroom villa with a balcony, and it's the only one with free cancellation. Rosen Inn at Pointe Orlando costs $916, or $131 a night, and scores 8.1 from 4,717 reviews. Two of the three are in the Universal Orlando area, where you can walk to Universal Studios, Islands of Adventure and Epic Universe. International Drive puts outlet malls and restaurants nearby.
B&B HOTEL Orlando International Drive near Universal - Newly Renovated!
£598 for 7 nights, two guests · £85 a night
See roomsSheraton Vistana Villages Resort Villas, I-Drive Orlando
£1,062 for 7 nights, two guests · £152 a night
See roomsRosen Inn at Pointe Orlando
£690 for 7 nights, two guests · £99 a night
See roomsAll hotels in Orlando for these dates
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
Where in Orlando
- Walt Disney World Resort: On-site hotels with early park entry and free transport.
- Lake Buena Vista: Hotels a short shuttle from Disney with lower rates.
- Universal Orlando area: Walkable to Universal Studios, Islands of Adventure and Epic Universe.
- International Drive: Central strip with outlet malls, restaurants and attractions.
- Kissimmee: Vacation villas with private pools for larger families.
What to do in Orlando
- Watch the fireworks over Cinderella Castle at Magic Kingdom.
- Ride Hagrid's Magical Creatures Motorbike Adventure at Universal.
- Give a full day to the Epic Universe park.
- Spend a day eating and wandering at EPCOT's World Showcase.
- Take a kayak or airboat tour on the Wekiva River for a break from the parks.
Also worth it
- Explore the Epic Universe park
- Spend a day at EPCOT's World Showcase
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 Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in Orlando | Orlando International (MCO), Orlando Sanford International (SFB) |
| Flight time | 11h (1 stop) |
| Distance | 993 miles each way |
| Time difference | +1 hour |
What 7 nights in Orlando costs
| Estimate | |
|---|---|
| Flights for two | £399 |
| Hotel, 7 nights (B&B HOTEL Orlando International Drive near Universal - Newly Renovated!) | £598 |
| Food, getting around and tickets, 7 days for two | £1,372 |
| Total for two | £2,369 |
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: Chicago to Orlando
| Per person | |
|---|---|
| This trip | £200 per person |
| Lowest in the last 30 days | £197 (14 Oct 2026) |
| Typical price, last 60 days | £222 |
| Price checks | 15 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Orlando.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars.
- Orlando is 1 hour ahead of Chicago.
- The $265 fare leaves O'Hare (ORD) and has one stop. A nonstop F9 option was $289 per person.
- The return flight leaves at 6:40 AM on Saturday, Nov 21, so plan for an early start.
- All three hotels are room only. Only the Sheraton has free cancellation.
Questions readers ask
How much is the flight?
We found $265 per person round trip, $529 for two, on F9 with one stop from Chicago O'Hare to Orlando International. That's all-in as found when we checked. Prices change.
Is there a nonstop?
Yes. When we checked, a nonstop F9 fare was $289 per person, $577 for two. That's $24 more per person than the one-stop fare.
What is the weather like?
Seasonal normals for these dates show highs of 74–78°F and lows between 58°F and 62°F. Expect mostly overcast days, with some clear and partly cloudy ones mixed in.
Do I need a passport?
No. This is a domestic trip from Chicago to Orlando, and you'll be paying in US dollars.
Is 7 nights enough?
For most people, yes. A week gives you time for Magic Kingdom, EPCOT, Universal and Epic Universe, with room left over for a Wekiva River tour or a slower day on International Drive.
What will the whole trip cost for two?
Our sample budget is $3,143 for two: $530 for flights, $793 for the best-value hotel and $1,820 for spending over 7 days.
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All trips from Chicago · Orlando from every city · Prices on this route · Trips in November 2026 · Home
Orlando in pictures
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Duren Williams / Pexels, Pexels License
- Photo: Simon Steiner / Pexels, Pexels License
- Photo: Connor Scott McManus / Pexels, Pexels License