Orlando from Chicago, Oct 16–18: round trip from $280
When we checked, round-trip nonstop flights on Frontier from Chicago O'Hare to Orlando were $280 per person ($560 for two) for Oct 16–18, 2026, a 2-night weekend. The forecast shows highs of 74–93°F and a small chance of rain. Our best-value hotel, Westgate Town Center Resort, is $272 for the stay.
The flight
$310 $280 per person, round trip
the typical fare on this route
$560 for two, taxes and fees included · Frontier · nonstop · 2h 57m
Out Fri, Oct 16, 8:11 PM – Sat, Oct 17, 12:08 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $280 | nonstop | 2h 57m |
| Frontier | $310 | 1 stop | 9h 18m |
| Frontier | $305 | 1 stop | 8h 53m |
Prices checked Oct 12, 2026, 3:15 AM CDT. 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 | $560 |
| Westgate Town Center Resort, 2 nights | $272 |
| Trip total for two | $832 |
Regular: $892 You pay: $832 Saved: $60
the typical fare on this route.
Tweak this trip
Why go now
At $280 per person round trip, or $560 for two, this fare is $30 below the typical fare on this route. That typical fare is $310, based on 13 earlier checks, so this one is 10% under. Across the 12 offers we checked, fares ran from $280 to $449, so this is the low end of what's on sale right now. Our lowest check in the past 30 days was $263, so it isn't the lowest we've seen, but it's a good price for a nonstop. October brings the EPCOT Food & Wine Festival and Halloween events, so a short weekend already has a plan. The forecast shows 93°F on Friday, 82°F on Saturday and 74°F on Sunday, with rain chances between 18% and 23%. Prices include taxes and fees as found and can change.
The kind of trip this is
This is a theme-park weekend with a festival twist. You'll fly in late Friday, spend Saturday in a park and have Sunday for a second park or something slower. It suits couples or friends who like a full day and don't mind a late arrival. It's also a decent fit for a family that picks one park and sticks with it. Expect a fast pace on Saturday and an easier Sunday.
Weather in Orlando, Oct 16–18
Highs 74–93°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 93 °F | 76 °F | 23% |
| Sat, Oct 17 | 82 °F | 74 °F | 22% |
| Sun, Oct 18 | 74 °F | 73 °F | 18% |
Where to stay in Orlando
Westgate Town Center Resort is our best-value pick. It's $272 for the 2 nights ($136 a night) for a Deluxe Studio Villa in Celebration, with a review score of 8.5 from 1,753 reviews. Wyndham I-Drive Avanti Resort & Conference Center is $259 for the stay ($130 a night) for a room with two queen beds. It scores 7.4 across 11,415 reviews and sits in the Universal Orlando area, which is walkable to Universal Studios, Islands of Adventure and Epic Universe. Baymont by Wyndham Orlando North Millenia is the budget choice at $128 for the stay ($64 a night), with breakfast included and a 6.8 score from 2,004 reviews. All three offered free cancellation when we checked. International Drive is the central strip if you want outlet malls and restaurants close by.
Westgate Town Center Resort
$272 for 2 nights, two guests · $136 a night
See roomsWyndham I-Drive Avanti Resort & Conference Center
$259 for 2 nights, two guests · $130 a night
See roomsBaymont by Wyndham Orlando North Millenia
$128 for 2 nights, two guests · $64 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 on Saturday night.
- Ride Hagrid's Magical Creatures Motorbike Adventure at Universal.
- Explore the Epic Universe park, walkable from the Universal Orlando area.
- Spend a day at EPCOT's World Showcase while the Food & Wine Festival is on.
- Take a kayak or airboat tour on the Wekiva River for a slower Sunday.
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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 | 2h 57m nonstop |
| Distance | 993 miles each way |
| Time difference | +1 hour |
What 2 nights in Orlando costs
| Estimate | |
|---|---|
| Flights for two | $560 |
| Hotel, 2 nights (Westgate Town Center Resort) | $272 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,352 |
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 | $280 per person |
| Lowest in the last 30 days | $263 (Oct 12, 2026) |
| Typical price, last 60 days | $310 |
| Price checks | 13 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- EPCOT Food & Wine Festival and Halloween events
- No passport is needed, and you'll pay in US dollars.
- Orlando is 1 hour ahead of Chicago. The outbound flight takes 2h 57m and covers 993 miles.
- The nonstop leaves O'Hare at 8:11 PM on Friday, Oct 16 and lands at 12:08 AM on Saturday, Oct 17.
- We didn't get return flight times for Sunday, Oct 18, so check them on the airline's site before you book.
- October brings the EPCOT Food & Wine Festival and Halloween events.
Questions readers ask
How much is the flight?
We found $280 per person round trip, or $560 for two, on a Frontier nonstop from O'Hare to Orlando International. That's $30 below the typical fare on this route. Prices include taxes and fees as found and can change.
What would the whole weekend cost for two?
Our sample budget comes to $1,352 for two: $560 for flights, $272 for 2 nights at Westgate Town Center Resort and $520 for spending.
Do I need a passport?
No. It's a domestic trip, and you'll pay in US dollars. Just keep in mind that Orlando runs 1 hour ahead of Chicago.
What is the weather like?
The forecast shows 93°F with drizzle on Friday, 82°F with showers on Saturday and 74°F with drizzle on Sunday. Rain chances run 18% to 23%, and lows stay between 73°F and 76°F.
Is 2 nights enough?
It's enough for one full park day plus a second park or a Wekiva River tour. The flight lands at 12:08 AM Saturday, so Friday is just travel.
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Image credits
- Photo: Simon Steiner / Pexels, Pexels License
- Photo: Connor Scott McManus / Pexels, Pexels License
- Photo: Duren Williams / Pexels, Pexels License