Chicago from Denver, Oct 16–18: round trip from $354
Round-trip flights from Denver to Chicago are $354 per person ($708 for two) for Oct 16–18, 2026, 2 nights, nonstop on Frontier. The forecast shows highs of 52–62°F and only a small chance of rain after Friday. The best-value hotel we found is $501 for the stay.
The flight
$354 per person, round trip
$708 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 | $354 | nonstop | 2h 29m |
| Frontier | $407 | 1 stop | 11h 42m |
| Frontier | $408 | 1 stop | 10h 50m |
Prices checked Oct 12, 2026, 6:28 PM MDT. 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 | $708 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $501 |
| Trip total for two | $1,209 |
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Why go now
$354 per person round trip, $708 for two, nonstop on Frontier. That's $11 under the $365 median of our 8 earlier checks on this route, or 3% less. It isn't a dramatic drop, and the lowest we saw was $336 on Oct 13, but a nonstop at this price for a weekend this close is solid value. The weather looks kind: Friday is overcast with a 60% chance of rain, then Saturday and Sunday turn mostly clear to clear with a 1% chance, highs from 52°F to 62°F. That's jacket weather, good for walking The Loop, a river architecture cruise and an afternoon at the Art Institute. Our rough budget for two comes to $1,729 with the lowest-priced hotel and $520 of spending money. Prices are all-in as we found them and can change before you book.
The kind of trip this is
A city weekend built on architecture, museums, deep-dish and live music. It suits a couple or a pair of friends who like to walk a lot, eat well and stay out for a blues set. The pace is quick: you land late Friday, then have Saturday and Sunday to pack in the river, the parks and the food. Bring layers for cool fall air.
Weather in Chicago, Oct 16–18
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 60% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value at $501 for the 2-night stay ($251 a night), with a 7.5 review score from 224 reviews. Heads-up: it sits by Midway, while the flight lands at O'Hare. River Hotel is the top rated at 8.3 from 7,928 reviews, $994 for the stay or $497 a night. Club Quarters Hotel Central Loop, Chicago is the lower-priced Loop option at $917 ($459 a night), scoring 8.2 from 5,337 reviews. Both of those are in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. All three rates are room only and none has free cancellation. If you'd rather be near nightlife, River North has galleries and steakhouses, and West Loop has the restaurant row on Randolph Street.
Holiday Inn Chicago Midway Airport S by IHG
$501 for 2 nights, two guests · $251 a night
See roomsRiver Hotel
$994 for 2 nights, two guests · $497 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$917 for 2 nights, two guests · $459 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 clear Saturday
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend an afternoon at the Art Institute of Chicago
- 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 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 | $708 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $501 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,729 |
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 | $354 per person |
| Lowest in the last 30 days | $336 (Oct 13, 2026) |
| Typical price, last 60 days | $365 |
| Price checks | 8 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and you pay in US dollars.
- Chicago is 1 hour ahead of Denver.
- The flight covers 919 miles in 2h 29m, leaving Denver at 8:55 PM Friday and landing at O'Hare at 12:24 AM Saturday.
- All three hotel rates are room only, with no free cancellation.
- Prices are all-in, taxes and fees included, as found when we checked; they can change.
Questions readers ask
How much is the flight?
$354 per person round trip, $708 for two, nonstop on Frontier from Denver International (DEN) to Chicago O'Hare (ORD). That's $11 under the $365 median of our earlier checks. The price was all-in when we found it and may change.
Do I need a passport?
No. It's a domestic trip, and the currency is the US dollar. Just note that Chicago runs 1 hour ahead of Denver.
What is the weather like?
Friday is overcast, 56°F high and 46°F low, with a 60% chance of rain. Saturday is mostly clear at 52°F, and Sunday is clear at 62°F, both with a 1% chance of rain.
Is 2 nights enough?
For a fast city weekend, yes. You land at 12:24 AM Saturday, so plan on Saturday and Sunday for the river cruise, Millennium Park, the Art Institute and a deep-dish dinner.
What will the whole weekend cost?
Our rough budget for two is $1,729: $708 for flights, $501 for the best-value hotel and $520 of spending money, which works out to $130 per person per day.
Can I cancel the hotel?
Not for free at the rates we found. Holiday Inn Chicago Midway Airport S by IHG, River Hotel and Club Quarters Hotel Central Loop, Chicago all show no free cancellation, and all three are room only.
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Image credits
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- Photo: Joshua Santos / Pexels, Pexels License
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