Chicago from Orlando, Oct 16–18: round trip from $270
Chicago from Orlando is $270 per person round trip for Oct 16–18, 2026 (2 nights), nonstop on Frontier, at the price we found when we checked. Expect highs of 53–62°F with little rain after a drizzly Friday. The best-value hotel, Club Quarters Hotel Central Loop, Chicago, is $917 for the stay.
The flight
$295 $270 per person, round trip
the typical fare on this route
$540 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 | $270 | nonstop | 3h 11m |
| Frontier | $310 | 1 stop | 10h 17m |
| Frontier | $270 | nonstop | 3h 18m |
Prices checked Oct 12, 2026, 3:04 PM EDT. 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 | $540 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights | $917 |
| Trip total for two | $1,457 |
Regular: $1,507 You pay: $1,457 Saved: $50
the typical fare on this route.
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Why go now
At $270 per person round trip, this nonstop Frontier fare is $25 below the typical fare on this route. That's 8% under the $295 median of our earlier checks. It also carries the "Lowest in 30 days" badge, and across 12 offers we saw fares from $270 to $339 per person. Flights for two come to $540. Add the Club Quarters room and $520 of spending money, and our planning total for the weekend is $1,977 for two. The forecast calls for jacket weather: a 51% chance of drizzle Friday with a high of 57°F, then clear skies Saturday at 53°F and Sunday at 62°F. That's good walking weather for a city made for walking, with museums, river views and deep-dish to fill the gaps. Prices were all-in when we checked, and they can change.
The kind of trip this is
This is a city getaway built around architecture, museums, food and live music, all packed into two nights. It suits a couple or a pair of friends who like to walk all day, eat well and stay out a little late. Friday moves fast after the early landing, and Saturday and Sunday are clear and more relaxed. Bring layers, since this is a cool-weather trip.
Weather in Chicago, Oct 16–18
Highs 53–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 57 °F | 46 °F | 51% |
| Sat, Oct 17 | 53 °F | 45 °F | 2% |
| Sun, Oct 18 | 62 °F | 46 °F | 2% |
Where to stay in Chicago
Club Quarters Hotel Central Loop, Chicago is the best-value pick at $917 for the 2 nights ($459 a night) for a Standard Queen Room. It's rated 8.2 from 5,337 reviews. River Hotel is the top-rated of the three at 8.3 from 7,925 reviews, $994 for the stay ($497 a night) for a Small Queen Room. Both are in The Loop, which puts architecture, theaters and Millennium Park right outside the door. 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. It's the only one of the three with free cancellation. The West Loop is converted warehouses and the restaurant row on Randolph Street. All three are room only.
Club Quarters Hotel Central Loop, Chicago
$917 for 2 nights, two guests · $459 a night
See roomsRiver Hotel
$994 for 2 nights, two guests · $497 a night
See roomsHotel Chicago West Loop, SureStay Collection by Best Western
$685 for 2 nights, two guests · $343 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 for the skyline from the water.
- See the Bean and the fountains in Millennium Park, a short walk from both Loop hotels.
- Spend clear, cool Saturday morning at the Art Institute of Chicago.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Hear live blues at Kingston Mines on Saturday night.
- Walk Lincoln Park for the free zoo and the lakefront.
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 | $540 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $917 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,977 |
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 | $270 per person |
| Lowest in the last 30 days | $270 (Oct 12, 2026) |
| Typical price, last 60 days | $295 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed: it's a domestic trip and the currency is the US dollar.
- Chicago is 1 hour behind Orlando.
- The nonstop takes 3h 11m to cover 986 miles from Orlando International (MCO) to Chicago O'Hare (ORD).
- All three hotels are room only, and only the SureStay has free cancellation.
- Prices include taxes and fees as we found them, and they can change before you book.
Questions readers ask
How much is the flight?
It's $270 per person round trip, or $540 for two, nonstop on Frontier from MCO to O'Hare. The outbound we found leaves Friday, Oct 16 at 5:20 AM and lands at 7:31 AM. A 4:44 PM flight landing at 7:02 PM was the same price.
Is $270 a good price for this route?
Yes. Our earlier checks put the typical fare at $295, so this one is 8% lower. Across 12 offers, fares ran from $270 to $339 per person.
Do I need a passport?
No. Chicago is a domestic trip from Orlando, so you won't need one, and you'll pay in US dollars.
What is the weather like?
Cool and mostly dry. Friday has a 51% chance of drizzle and a high of 57°F. Saturday is clear at 53°F and Sunday clear at 62°F, with lows of 45–46°F, so pack a warm layer.
Is 2 nights enough?
For a first visit, yes. The 5:20 AM flight gets you in with most of Friday ahead. Two more days are enough for the river cruise, Millennium Park, the Art Institute, a deep-dish dinner and a blues night.
What does the whole weekend cost?
Our planning total is $1,977 for two: $540 for flights, $917 at Club Quarters Hotel Central Loop, Chicago and $520 of spending money.
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Chicago in pictures
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Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License