Chicago from Denver, 16 – 18 Oct: £911 for two, all in
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The verdict
Our verdict
Worth it, if
- Frontier nonstop, 2h 29m, $354 per person round trip
- Fare is $11 under the $365 typical on this route
- Saturday mostly clear at 52°F, Sunday clear at 62°F
The catch: The value hotel is by Midway Airport, not downtown, your flight lands at O'Hare at 12:24 AM, and no hotel offered free cancellation.
Worth it if you want a quick city weekend of museums, deep-dish and blues; skip it if landing after midnight would wreck your Saturday.
Worth it if you don't mind a late Friday arrival: $1,209 for two covers the flights at $708 plus the hotel at $501, taxes and fees included, for Oct 16–18, 2026, 2 nights. Frontier flies nonstop from Denver to O'Hare in 2h 29m, leaving at 8:55 PM Friday and landing at 12:24 AM Saturday. A checked bag, resort fees and spending money aren't in that total.
The total, before you go
£911 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £534 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £378 |
| The total, before you go | £911 |
| Hold luggage each, return (not in the total) | about £181 |
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
£267 per person, return
£534 for two, taxes and fees included · Frontier · nonstop · 2h 29m
Out Fri, Oct 16, 8:55 PM – Sat, Oct 17, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £267 | nonstop | 2h 29m |
| Frontier | £307 | 1 stop | 11h 42m |
| Frontier | £308 | 1 stop | 10h 50m |
Prices checked 12 Oct 2026, 18:28 GMT-6. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $354 per person, the nonstop fare is $11 below the $365 median of our 8 earlier checks on this route, about 3% under. That puts the trip at $1,209 for two with the Holiday Inn Chicago Midway Airport S by IHG, taxes and fees included; a checked bag, resort fees and spending money come on top. The forecast works in your favor: Friday is overcast with a 60% chance of rain, but you land just after midnight, and Saturday turns mostly clear with a high of 52°F, then clear on Sunday at 62°F. That's jacket weather for the architecture river cruise and a long walk through Millennium Park. Chicago is 919 miles away and one hour ahead of Denver, and the 8:55 PM Friday departure keeps your workday intact.
The kind of trip this is
A fast city weekend built around architecture, museums, deep-dish and live blues. It suits a couple or two friends who like to walk a lot and eat well, with a short Saturday morning and two days to fill. The pace is brisk: one big museum, one boat ride, one late night of music, then home.
Weather in Chicago, 16 – 18 Oct
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 56 °F | 46 °F | 60% |
| Sat 17 Oct | 52 °F | 44 °F | 1% |
| Sun 18 Oct | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the value pick at $501 for the 2 nights ($251 a night), rated 7.5 from 224 reviews, in a Standard King Room. It keeps the trip at $1,209, but it sits by Midway Airport while your flight lands at O'Hare, so plan the ride. If you'd rather step out into The Loop, with architecture, theatres and Millennium Park close by, River Hotel is the top rated at 8.3 from 7,928 reviews, $994 for the stay ($497 a night) in a Small Queen Room. Club Quarters Hotel Central Loop, Chicago is the lower-priced Loop option at $917 ($459 a night), rated 8.2 from 5,337 reviews. None of the three offered free cancellation when we checked.
Holiday Inn Chicago Midway Airport S by IHG
£378 for 2 nights, two guests · £189 a night
See roomsRiver Hotel
£749 for 2 nights, two guests · £375 a night
See roomsClub Quarters Hotel Central Loop, Chicago
£691 for 2 nights, two guests · £346 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 mostly clear Saturday
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend Sunday at 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 Denver | Denver International (DEN) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 29m nonstop |
| Distance | 919 miles each way |
| Time difference | +1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £534 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £378 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,303 |
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: Denver to Chicago
| Per person | |
|---|---|
| This trip | £267 per person |
| Lowest in the last 30 days | £253 (13 Oct 2026) |
| Typical price, last 60 days | £275 |
| Price checks | 8 |
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 one hour ahead of Denver; the 8:55 PM departure lands at 12:24 AM local time.
- The flight is 2h 29m nonstop, 919 miles, from Denver International (DEN) to Chicago O'Hare International (ORD).
- The $1,209 total covers flights and the Holiday Inn room only, taxes and fees in; a checked bag, resort fees and spending money are extra.
- Prices were all-in when we checked and can change; none of the three hotels offered free cancellation.
Questions readers ask
Is it worth it?
Worth it if a short city weekend fits you. The fare is $354 per person, $11 below the $365 typical, the flight is a 2h 29m nonstop, and Saturday and Sunday look clear. The trade-offs are a 12:24 AM arrival and a value hotel by Midway Airport rather than downtown.
How much is the whole trip for two?
$1,209 for two: $708 for the Frontier flights plus $501 for 2 nights at Holiday Inn Chicago Midway Airport S by IHG, taxes and fees included when we checked. A checked bag, resort fees and spending money are not in it.
What is the weather like?
Friday, Oct 16 is overcast with a 56°F high and a 60% chance of rain. Saturday is mostly clear, 52°F high and 44°F low, and Sunday is clear at 62°F, both with a 1% chance of rain. Pack a warm layer.
Is 2 nights enough?
For a first taste, yes, with a plan. You land at 12:24 AM Saturday, so you get Saturday plus Sunday until your flight home: a river cruise, Millennium Park, the Art Institute, deep-dish and one night of blues.
Do I need a passport?
No. It's a domestic trip from Denver International (DEN) to Chicago O'Hare International (ORD), and you'll pay in US dollars.
Which airport do I land at?
Chicago O'Hare International (ORD). The value hotel is by Chicago Midway International (MDW), the city's other airport, so allow time for the ride after a 12:24 AM landing, or pick one of the two Loop hotels.
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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