Chicago from Orlando, 16 – 18 Oct: £1,098 for two, all in
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The verdict
Our verdict
Worth it, because
- Nonstop on Frontier, 3h 11m, landing at O'Hare 7:31 AM Friday
- $270 per person, $25 below the typical fare on this route
- Club Quarters in The Loop scores 8.2 from 5,337 reviews
The catch: Frontier's fare doesn't include a checked bag, which runs about $240 for two, and the 5:20 AM departure means a very early Friday.
Worth it if you pack light and want a city weekend of museums, food and blues; skip it if a 5:20 AM flight is a dealbreaker.
Worth it for the two of you. The trip is $1,457 for two, all in: nonstop Frontier flights at $540 plus 2 nights at Club Quarters Hotel Central Loop, Chicago at $917, taxes and fees included. You fly out Friday, Oct 16 and come home Sunday, Oct 18, 2026, and a checked bag and spending money aren't in that total.
The total, before you go
£1,098 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £407 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £691 |
| The total, before you go | £1,098 |
| Hold luggage each, return (not in the total) | about £181 |
£19 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
£204 per person, return
£407 for two, taxes and fees included · Frontier · nonstop · 3h 11m
Out Fri, Oct 16, 5:20 AM – Fri, Oct 16, 7:31 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £204 | nonstop | 3h 11m |
| Frontier | £234 | 1 stop | 10h 17m |
| Frontier | £204 | nonstop | 3h 18m |
Prices checked 12 Oct 2026, 15:04 GMT-4. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $270 per person, this nonstop is $25 below the typical fare on this route, a gap of 8%, and it's the lowest fare in 30 days of our checks. Across the 12 offers we checked, fares ran from $270 to $339 per person. That brings the whole trip to $1,457 for two, all in, covering the flights and two nights at Club Quarters Hotel Central Loop, Chicago. A checked bag and spending money are extra. Mid-October works for a city weekend. The forecast shows drizzle Friday, with a 51% chance of rain and a high of 57°F, then clear skies Saturday and Sunday with highs of 53°F and 62°F. That's jacket weather for walking the river and the Loop, and the Art Institute covers the damp first day. These prices are what we found when we checked, and they can change.
The kind of trip this is
This is a quick city weekend for two: architecture seen from the river, a major art museum, deep-dish and a night of live blues. The pace is full but walkable if you stay in The Loop, and you'll spend much of Friday arriving early and settling in. It suits couples or a pair of friends who'd rather spend a weekend on food, museums and a late night out than on lounging.
Weather in Chicago, 16 – 18 Oct
Highs 53–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 57 °F | 46 °F | 51% |
| Sat 17 Oct | 53 °F | 45 °F | 2% |
| Sun 18 Oct | 62 °F | 46 °F | 2% |
Where to stay in Chicago
Our pick is Club Quarters Hotel Central Loop, Chicago. It's the best value at $917 for the 2 nights ($459 a night), rated 8.2 from 5,337 reviews, for a Standard Queen Room, and it's the hotel in the total. River Hotel is the top rated at 8.3 from 7,925 reviews and costs $994 for the stay ($497 a night). It's also in the Loop. On a budget, Hotel Chicago West Loop, SureStay Collection by Best Western is $685 for the stay ($343 a night), rated 7.4 from 877 reviews, and it's the only one of the three with free cancellation. In The Loop you have architecture, theaters and Millennium Park at your doorstep, and West Loop has the restaurant row on Randolph Street.
Club Quarters Hotel Central Loop, Chicago
£691 for 2 nights, two guests · £346 a night
See roomsRiver Hotel
£749 for 2 nights, two guests · £375 a night
See roomsHotel Chicago West Loop, SureStay Collection by Best Western
£516 for 2 nights, two guests · £259 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 on Saturday, when the forecast is clear
- See the Bean and the fountains in Millennium Park, close to the Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend drizzly Friday afternoon inside the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
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 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 | £407 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £691 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,490 |
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 | £204 per person |
| Lowest in the last 30 days | £204 (12 Oct 2026) |
| Typical price, last 60 days | £222 |
| Price checks | 6 |
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).
- No passport needed: it's a domestic trip, paid in US dollars.
- Chicago is 1 hour behind Orlando.
- The nonstop from MCO to Chicago O'Hare International (ORD) covers 986 miles in 3h 11m.
- The total doesn't include a checked bag (about $240 for two) or any resort fee the hotel charges.
- Club Quarters and River Hotel don't offer free cancellation, but the SureStay in West Loop does.
Questions readers ask
Is it worth it?
Yes, for most travelers. You get a nonstop at $270 per person, $25 below the typical fare on this route, a Loop hotel rated 8.2 and clear skies forecast for Saturday and Sunday. The trade-offs are a 5:20 AM departure and bags that cost extra.
How much is the whole trip for two?
It's $1,457 for two, all in: $540 for the flights and $917 for 2 nights at Club Quarters Hotel Central Loop, Chicago, taxes and fees included. A checked bag adds about $240 for two. We budget $520 in spending money for the two days, which brings the trip to $1,977.
Is there a later flight than 5:20 AM?
Yes. We also found a Frontier nonstop that leaves at 4:44 PM and lands at 7:02 PM for the same $270 per person. You skip the early alarm but give up most of Friday in Chicago.
What is the weather like?
Friday, Oct 16 calls for drizzle, a 51% chance of rain and temperatures from 46°F to 57°F. Saturday looks clear, 45°F to 53°F, and Sunday looks clear too, 46°F to 62°F. Bring a warm layer and a light rain jacket.
Is 2 nights enough?
For a first look, yes. The early flight lands at 7:31 AM Friday, so you have time for the Art Institute and Millennium Park that day. Saturday works for the river cruise and the blues, and Sunday for deep-dish before you head home.
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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 15 Oct 2026.
Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License