Chicago from Orlando, Oct 23–25: $1,208 for two, all in
The verdict
Our verdict
Worth it, because
- Nonstop on Frontier, 3h 11m
- $32 per person below the typical fare on this route
- Lowest in 30 days on this route
The catch: Seat picks on basic fares and a checked bag (about $240 for two, round trip) 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.
Nonstop flights on Frontier from Orlando to Chicago cost $258 per person for Oct 23–25, 2026 when we checked, $32 below the typical fare on this route. Three places to stay start at $282 a night for the 2-night stay. The total, before you go: $1,113 for two, flights and Aloft by Marriott Chicago Mag Mile with taxes and fees. Prices move; every link below shows the live price.
The total, before you go
$1,208 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $516 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | $597 |
| Resort fee, collected at the desk | $95 |
| The total, before you go | $1,208 |
| A checked bag each, round trip (not in the total) | about $240 |
$32 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); 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
$258 per person, round trip
$516 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 | $258 | nonstop | 3h 11m |
| Frontier | $342 | 1 stop | 8h |
| Frontier | $258 | nonstop | 3h 18m |
Prices checked Oct 15, 2026, 10:59 PM EDT. 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 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, Oct 23–25
Highs 68–72°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 72 °F | 59 °F | 5% |
| Sat, Oct 24 | 69 °F | 58 °F | 5% |
| Sun, Oct 25 | 68 °F | 58 °F | 12% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$630 for 2 nights, two guests · $315 a night
See roomsCongress Plaza Hotel Chicago
$563 for 2 nights, two guests · $282 a night
See roomsAll hotels in Chicago 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 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
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 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 | $516 |
| Hotel, 2 nights (Aloft by Marriott Chicago Mag Mile) | $597 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,633 |
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 | $258 per person |
| Lowest in the last 30 days | $258 (Oct 16, 2026) |
| Typical price, last 60 days | $290 |
| Price checks | 9 |
Good to know
- Passport: no passport needed for travelers 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 $1,633 for two: $516 in flights, $597 for the hotel and $520 for food, getting around and tickets.
What is the weather like in Chicago Oct 23–25?
Highs 68–72°F, little rain expected
Do I need a passport for Chicago?
No. No passport needed for travelers 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 $258 a good price for Orlando to Chicago?
It is 11% below the typical $290 per person we see on this route, which is why it made the list.
Also found for you
The newest finds from Orlando.
Just found · from Orlando
Mexico City
Nov 5–9, 2026 · 4 nights
- Nonstop from MCO, leaving 5:05 PM and landing 7:45 PM local
- $388 per person, $30 below the typical fare on this route
- Highs of 76–78°F, good weather for museums and walking the city
$1,279 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
Flights $775 + hotel $433 + resort fee $71, taxes in · a checked bag each adds about $160
Volaris · nonstop · 6h 48m
The catch: You'll need a passport, Hotel Casa Anzures doesn't offer free cancellation, and a checked bag costs about $160 for two on top of the total.
Worth it if you want museums, tacos and long city walks; skip it if you're after a beach or a pool.
Tweak this trip
Just found · from OrlandoLowest in 30 daysWorth it, if
Sedona
Nov 14–21, 2026 · 7 nights
- Fare is $227 per person, $33 below the typical fare
- Cowboy Hideout scores 9.6 from 19 reviews, with free cancellation
- Peak hiking season: highs 55–66°F, lows near 39°F
$1,473 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights $454 + hotel $904 + resort fee $115, taxes in · a checked bag each adds about $240
Frontier · with a stop · 8h 10m
The catch: Frontier makes one stop and takes 8h 10m to Phoenix, Sedona is two hours north, and checked bags run about $240 for two.
Worth it if you want a week of red-rock hiking in cool weather; skip it if a stop plus a two-hour drive feels like too much.
Tweak this trip
Just found · from OrlandoNot worth it this week
Kyoto & Osaka
Dec 11–16, 2026 · 5 nights
- Comfort Hotel ERA Kyoto Horikawagojo: 8.8 from 4,312 reviews, $53 a night
- Free cancellation at all three hotels we picked
- December highs of 48–56°F, good for temple walks in a coat
$3,196 for two · 5 nights · flights, hotel, taxes & fees
Flights $2,931 + hotel $265, taxes in · a checked bag each adds about $240
F9 + YP + MM · with a stop · 64h 6m
The catch: The fare is $1,466 per person against a typical $1,187, with 3 stops, and you land Sunday, Dec 13 at 9:15 AM.
Worth it if these dates are fixed and long layovers don't bother you; skip it if you can wait for a fare closer to $1,187.
Tweak this trip
More trips
Just found · from Orlando
Nashville
Oct 23–25, 2026 · 2 nights
- Nonstop on Frontier, 2h 13m
- $25 per person below the typical fare on this route
- Best Western Plus Nashville Airport Hotel - BNA, rated 8.1 by 1,348 guests
$1,097 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $630 + hotel $405 + resort fee $62, taxes in · a checked bag each adds about $240
Frontier · nonstop · 2h 13m
The catch: Seat picks on basic fares and a checked bag (about $240 for two, round trip) 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.
The weekend after · from OrlandoLowest in 30 daysWorth it, if
Bermuda
Oct 30–Nov 1, 2026 · 2 nights
- $531 per person, $402 below the typical fare on this route
- American, one stop, leaves Orlando 8:00 AM and lands 3:09 PM
- Typical highs of 76–77°F, lows near 73°F for these dates
$1,646 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,062 + hotel $501 + resort fee $83, taxes in · a checked bag each adds about $160
American · with a stop · 6h 9m
The catch: The flight out has one stop and takes 6h 9m, the weather normals show drizzle, and hurricane-season swells can close South Shore beaches.
Worth it if you want a low-key island weekend of walks, caves and rum swizzles; skip it if the trip only works with full beach days.
Nine nights away · from OrlandoLowest in 30 daysWorth it, if
Big Island (Kona & Hilo)
Nov 14–23, 2026 · 9 nights
- $604 per person, $130 below the typical fare on this route
- Kalani Kai#104 in walkable Kailua-Kona, rated 9 from 6 reviews
- Highs of 80–81°F and lows near 70°F for snorkeling and volcano days
$2,946 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,208 + hotel $1,501 + resort fee $237, taxes in · a checked bag each adds about $160
United · with a stop · 13h 24m
The catch: The outbound United flight has one stop and takes 13h 24m, and a checked bag is about $160 for two, which isn't in the total.
Worth it if a long travel day is fine for nine nights of volcanoes and snorkeling; skip it if you need a nonstop or free cancellation.
Just found · from Orlando
Mexico City
Nov 5–9, 2026 · 4 nights
- Nonstop from MCO, leaving 5:05 PM and landing 7:45 PM local
- $388 per person, $30 below the typical fare on this route
- Highs of 76–78°F, good weather for museums and walking the city
$1,279 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
Flights $775 + hotel $433 + resort fee $71, taxes in · a checked bag each adds about $160
Volaris · nonstop · 6h 48m
The catch: You'll need a passport, Hotel Casa Anzures doesn't offer free cancellation, and a checked bag costs about $160 for two on top of the total.
Worth it if you want museums, tacos and long city walks; skip it if you're after a beach or a pool.
All trips from Orlando · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.
Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License