Chicago from Des Moines, Oct 16–18: $1,928 for two, all in
The verdict
Our verdict
Not worth it this week
- $504 per person, $185 below the typical fare on this route
- United and American nonstops at $587 per person, 96 to 101 minutes
- Club Quarters in The Loop, rated 8.2 from 5,335 reviews
The catch: The $504 Frontier fare has one stop and takes 27h 59m, landing at 12:24 AM on Sunday, Oct 18, the day the trip ends.
Worth it if you switch to a $587 nonstop and want a walkable Loop weekend; skip the Frontier fare entirely.
Not worth it this week. The $1,928 total for two includes Frontier flights at $1,008 and Club Quarters Hotel Central Loop, Chicago at $794 plus its $126 property fee, with taxes and fees included, but that fare gets you there too late. The trip is Oct 16–18, 2026, for 2 nights, and the Frontier flight isn't nonstop: it has one stop, takes 27h 59m and lands at 12:24 AM Sunday, the day you fly home, while the United and American nonstops we found were $587 per person.
The total, before you go
$1,928 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $1,008 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | $794 |
| Resort fee, collected at the desk | $126 |
| The total, before you go | $1,928 |
| A checked bag each, round trip (not in the total) | about $240 |
$185 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
$504 per person, round trip
$1,008 for two, taxes and fees included · Frontier · 1 stop · 27h 59m
Out Fri, Oct 16, 8:25 PM – Sun, Oct 18, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $504 | 1 stop | 27h 59m |
| American. Operated by Republic Airways as American Eagle | $587 | nonstop | 1h 41m |
| United | $587 | nonstop | 1h 36m |
Prices checked Oct 14, 2026, 8:32 PM CDT. Prices change; the binding price is the one on the booking site.
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Why now
At $504 per person, this fare is $185 below the typical fare on this route ($689), a gap of 27%. On paper, that makes it the value pick for the weekend. The schedule is the problem. Frontier leaves Des Moines at 8:25 PM on Friday, Oct 16, stops once and reaches O'Hare at 12:24 AM on Sunday, Oct 18, the same day the trip ends. That leaves you no real time in Chicago. The United and American nonstops we checked take 96 and 101 minutes and were $587 per person, which is still $102 below the typical fare. Expect mixed weather: a 78% chance of drizzle Friday, overcast and 57°F on Saturday, then clear and 63°F on Sunday. On the nonstop, it's a fair fall city weekend. On the Frontier fare, we'd pass. Prices are as we found them and can change.
The kind of trip this is
This is a short fall city weekend of architecture, museums, deep-dish and live blues, all within reach of a Loop hotel. It suits a couple or two friends who like to walk a city and eat well, and the pace is quick: two full-ish days at most. Bring a layer, since highs run 57°F to 63°F. It only works if you land by Friday morning.
Weather in Chicago, Oct 16–18
Highs 57–63°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 59 °F | 48 °F | 78% |
| Sat, Oct 17 | 57 °F | 43 °F | 13% |
| Sun, Oct 18 | 63 °F | 48 °F | 1% |
Where to stay in Chicago
All three picks are in The Loop, with architecture, theatres and Millennium Park at your doorstep. Club Quarters Hotel Central Loop, Chicago is the best value at $794 for 2 nights ($397 a night). It's rated 8.2 from 5,335 reviews and is room only with no free cancellation. Its $126 property fee is already in our total. River Hotel is the top rated, at 8.3 from 7,929 reviews. It's $929 for the stay ($465 a night), plus $148 paid at the property. La Quinta Inn & Suites by Wyndham Chicago Downtown is $812 ($406 a night) and rated 8.0 from 3,744 reviews. It's the only one with breakfast and free cancellation, plus $129 paid at the property. For dinner and drinks, River North has galleries, steakhouses and the city's nightlife.
Club Quarters Hotel Central Loop, Chicago
$794 for 2 nights, two guests · $397 a night
See roomsRiver Hotel
$929 for 2 nights, two guests · $465 a night
See roomsLa Quinta Inn & Suites by Wyndham Chicago Downtown
$812 for 2 nights, two guests · $406 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 rain chances drop to 13%
- See the Bean and the fountains in Millennium Park, a short walk from all three hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago, a good plan for drizzly Friday
- Hear live blues at Kingston Mines on Saturday night
Also worth it
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Des Moines | Des Moines International (DSM) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 27h 59m (1 stop) |
| Distance | 310 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,008 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $794 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,322 |
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: Des Moines to Chicago
| Per person | |
|---|---|
| This trip | $504 per person |
| Lowest in the last 30 days | $484 (Oct 14, 2026) |
| Typical price, last 60 days | $689 |
| Price checks | 12 |
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).
- No passport needed: it's a domestic trip, you pay in US dollars and there's no time difference from Des Moines.
- Chicago is 310 miles from Des Moines, and the nonstops take 96 to 101 minutes.
- A checked bag is about $240 for two and isn't in the $1,928 total. Spending money isn't either.
- Only La Quinta Inn & Suites by Wyndham Chicago Downtown offers free cancellation; the other two hotels don't.
- Chicago has two airports, O'Hare (ORD) and Midway (MDW). The fares we found fly into O'Hare.
Questions readers ask
Is it worth it?
Not at the Frontier fare. It's $504 per person, but it takes 27h 59m with one stop and lands at 12:24 AM on Sunday, Oct 18, the day you head home. A nonstop at $587 per person makes the weekend work.
How much is the whole trip for two?
$1,928 for two, with taxes and fees included: Frontier flights at $1,008, 2 nights at Club Quarters Hotel Central Loop, Chicago at $794 and its $126 property fee. A checked bag, about $240 for two, and spending money aren't included.
What about the nonstop flights?
When we checked, United and American had nonstops at $587 per person, or $1,174 for two. United leaves at 8:00 AM Friday and lands at 9:36 AM. American leaves at 7:29 AM and lands at 9:10 AM. That's still below the typical fare of $689 per person.
What is the weather like?
Friday has a 78% chance of drizzle, with a high of 59°F. Saturday is overcast and 57°F with a 13% chance of rain. Sunday looks clear at 63°F. Lows run 43°F to 48°F.
Do I need a passport?
No. It's a domestic trip in US dollars, and Chicago is on the same time as Des Moines.
Is 2 nights enough?
Yes, if you take a morning nonstop on Friday. That's enough for the river cruise, Millennium Park, the Art Institute and a blues night. On the Frontier fare you'd get almost no time in the city.
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All trips from Des Moines · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Image credits
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