Chicago from Des Moines, Oct 23–25: $1,652 for two, all in
The verdict
Our verdict
Worth it, if
- $153 per person below the typical fare on this route
- Highs 70–72°F, little rain expected
- No passport needed
The catch: Not nonstop: a stop on the way, 27h 59m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Round-trip flights on Frontier from Des Moines to Chicago cost $494 per person for Oct 23–25, 2026 when we checked, $153 below the typical fare on this route. Three places to stay start at $287 a night for the 2-night stay. The total, before you go: $1,561 for two, flights and Hilton Chicago with taxes and fees. Prices move; every link below shows the live price.
The total, before you go
$1,652 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $988 |
| Hilton Chicago, 2 nights, two guests, taxes in | $573 |
| Resort fee, collected at the desk | $91 |
| The total, before you go | $1,652 |
| A checked bag each, round trip (not in the total) | about $240 |
$153 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
$494 per person, round trip
$988 for two, taxes and fees included · Frontier · 1 stop · 27h 59m
Out Fri, Oct 23, 8:25 PM – Sun, Oct 25, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $494 | 1 stop | 27h 59m |
| United. Operated by SkyWest DBA United Express | $587 | nonstop | 1h 41m |
| American. Operated by Republic Airways as American Eagle | $587 | nonstop | 1h 41m |
Prices checked Oct 16, 2026, 2:42 AM CDT. 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
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Why Chicago
Why we picked it: Chicago is the best value we priced for the weekend: $494 round trip, 24% 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 70–72°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 70 °F | 57 °F | 5% |
| Sat, Oct 24 | 72 °F | 58 °F | 5% |
| Sun, Oct 25 | 70 °F | 58 °F | 12% |
Where to stay in Chicago
Hilton Chicago
$573 for 2 nights, two guests · $287 a night
See roomsL7 Chicago by LOTTE
$1,143 for 2 nights, two guests · $572 a night
See roomsAloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 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
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 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 | $988 |
| Hotel, 2 nights (Hilton Chicago) | $573 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,081 |
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 | $494 per person |
| Lowest in the last 30 days | $424 (Oct 16, 2026) |
| Typical price, last 60 days | $647 |
| Price checks | 27 |
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 Des Moines cost?
About $2,081 for two: $988 in flights, $573 for the hotel and $520 for food, getting around and tickets.
What is the weather like in Chicago Oct 23–25?
Highs 70–72°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 Des Moines to Chicago?
27h 59m with 1 stop on Frontier, on the fare we found.
Is $494 a good price for Des Moines to Chicago?
It is 24% below the typical $647 per person we see on this route, which is why it made the list.
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Las Vegas
Oct 30–Nov 1, 2026 · 2 nights
- Nonstop on Allegiant, 3h 14m, $144 below the typical fare per person
- Harrah's scores 7.9 from 10,371 reviews, with free cancellation
- Highs of 73–76°F, good weather for the Red Rock Canyon loop
$915 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $658 + hotel $230 + resort fee $27, taxes in · a checked bag each adds about $200
Allegiant · nonstop · 3h 14m
The catch: The outbound lands at 11:14 PM Friday, and a checked bag costs about $200 for two, which isn't in the $915 total.
Worth it if you want a packed weekend of shows, food and one desert drive; skip it if you want a slow, quiet getaway.
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Yosemite
Oct 23–25, 2026 · 2 nights
- Fare is $497 per person, $32 below the typical fare
- Studio rated 8.4 from 26 reviews, with free cancellation
- Saturday forecast: 69°F, partly cloudy, 7% chance of rain
$1,822 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $994 + hotel $740 + resort fee $88, taxes in · a checked bag each adds about $200
Allegiant · with a stop · 35h 47m
The catch: With one stop each way you spend 35h 47m traveling in total, landing Saturday at 10:17 AM and flying home Sunday at 8:51 PM.
Worth it if you'll trade long travel days for a packed Saturday among granite and sequoias; skip it if you want a relaxed weekend.
Tweak this trip
Just found · from Des Moines26% below typicalNot worth it this week
Chicago
Oct 16–18, 2026 · 2 nights
- $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
$1,928 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,008 + hotel $794 + resort fee $126, taxes in · a checked bag each adds about $240
Frontier · with a stop · 27h 59m
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.
Tweak this trip
More trips
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Las Vegas
Oct 23–25, 2026 · 2 nights
- Nonstop on Allegiant, 3h 14m, leaving Friday at 10:00 PM
- $268 per person below the highest fare we saw for these dates
- Horseshoe on the Strip: 7.9 from 8,089 reviews, free cancellation
$1,393 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $876 + hotel $462 + resort fee $55, taxes in · a checked bag each adds about $200
Allegiant · nonstop · 3h 14m
The catch: A checked bag is about $200 for two and resort fees aren't in the total, and you land at 11:14 PM Friday.
Worth it if you want shows, food and the Strip in mild weather; skip it if a late Friday arrival will drag you down.
The weekend after · from Des Moines26% below typicalWorth it, if
Asheville
Oct 30–Nov 1, 2026 · 2 nights
- $452 per person, $166 below the typical fare on this route
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$1,193 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $903 + hotel $260 + resort fee $30, taxes in · a checked bag each adds about $200
Allegiant · with a stop · 41h 23m
The catch: There's one stop each way and 41h 23m of travel in all: you land at 11:04 PM Friday and fly out at 6:00 AM Sunday.
Worth it if one full Saturday of foliage, breweries and bluegrass is enough for you; skip it if you want a slow, unhurried weekend.
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San Francisco
Nov 14–21, 2026 · 7 nights
- Royal Pacific Motor Inn in Chinatown: 8 from 1,943 reviews, free cancellation
- One stop, 5h 59m, landing at SFO by 9:29 AM day one
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$2,400 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
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United. Operated by SkyWest DBA United Express · with a stop · 5h 59m
The catch: One stop and 5h 59m out, leaving at 5:30 AM; a checked bag is about $160 for two, not in the total.
Worth it if you want a walkable food-and-views week for two; skip it if you need sun or a nonstop.
Just found · from Des MoinesLowest in 30 days
Las Vegas
Oct 30–Nov 1, 2026 · 2 nights
- Nonstop on Allegiant, 3h 14m, $144 below the typical fare per person
- Harrah's scores 7.9 from 10,371 reviews, with free cancellation
- Highs of 73–76°F, good weather for the Red Rock Canyon loop
$915 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $658 + hotel $230 + resort fee $27, taxes in · a checked bag each adds about $200
Allegiant · nonstop · 3h 14m
The catch: The outbound lands at 11:14 PM Friday, and a checked bag costs about $200 for two, which isn't in the $915 total.
Worth it if you want a packed weekend of shows, food and one desert drive; skip it if you want a slow, quiet getaway.
All trips from Des Moines · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License