Chicago from Detroit, Oct 16–18: $1,558 for two, all in
The verdict
Our verdict
Worth it, if
- $308 per person below the typical fare on this route
- Lowest in 30 days on this route
- La Quinta Inn & Suites by Wyndham Chicago Downtown, rated 8 by 3,744 guests
The catch: Not nonstop: a stop on the way, 8h 38m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Round-trip flights from Detroit to Chicago are $358 per person, or $716 for two, on Frontier for Oct 16–18, 2026, a 2-night weekend with 1 stop rather than nonstop. Expect highs of 58–65°F with drizzle likely on Friday, and La Quinta Inn & Suites by Wyndham Chicago Downtown is the best value at $842 for the stay, breakfast included.
The total, before you go
$1,558 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $716 |
| La Quinta Inn & Suites by Wyndham Chicago Downtown, 2 nights, two guests, taxes in | $842 |
| The total, before you go | $1,558 |
| A checked bag each, round trip (not in the total) | about $240 |
$308 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); 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
$358 per person, round trip
$716 for two, taxes and fees included · Frontier · 1 stop · 8h 38m
Out Fri, Oct 16, 3:01 PM – Fri, Oct 16, 10:39 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $358 | 1 stop | 8h 38m |
| American. Operated by Envoy Air as American Eagle | $511 | nonstop | 1h 34m |
| American. Operated by SkyWest Airlines as American Eagle | $511 | nonstop | 1h 40m |
Prices checked Oct 13, 2026, 3:50 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
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Why now
$358 per person round trip, or $716 for two, is $308 below the typical fare on this route, 46% under. The fare carries a Lowest in 30 days badge, and the 12 offers we checked ran from $358 to $531. The catch is time: the Frontier flight has 1 stop and takes 8h 38m to cover 237 miles, while an American nonstop ran $511 per person when we checked. Mid-October falls between the summer festival season and the holiday lights on Michigan Avenue, so this is a quieter city weekend. Friday looks drizzly with a 73% chance of rain, then Saturday and Sunday turn overcast with little rain in the forecast and highs of 58°F and 65°F. That's weather for museums, a river cruise and deep-dish, not the beach.
The kind of trip this is
This is a city weekend built around food, architecture and live music. It suits a couple or two friends who like to walk, eat well and duck into a museum when the clouds roll in. The pace is easy: a late Friday landing at 10:39 PM, one full day on Saturday and a slow Sunday, so keep the first night simple.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 59 °F | 47 °F | 73% |
| Sat, Oct 17 | 58 °F | 45 °F | 1% |
| Sun, Oct 18 | 65 °F | 49 °F | 2% |
Where to stay in Chicago
All three picks are in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. La Quinta Inn & Suites by Wyndham Chicago Downtown is the best value: $842 for 2 nights ($421 a night), a review score of 8 from 3,744 reviews, breakfast included and free cancellation. Canopy By Hilton Chicago Central Loop is the top rated at 8.9 from 308 reviews, $960 for the stay ($480 a night), room only and not free to cancel. Club Quarters Hotel Central Loop, Chicago sits between the other two at $893 ($447 a night), scoring 8.2 across 5,339 reviews, the most of the three, room only with no free cancellation. If you'd rather sleep near the bars, River North is the city's nightlife core.
La Quinta Inn & Suites by Wyndham Chicago Downtown
$842 for 2 nights, two guests · $421 a night
See roomsCanopy By Hilton Chicago Central Loop
$960 for 2 nights, two guests · $480 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 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 overcast, mostly dry Saturday.
- See the Bean and the fountains in Millennium Park, right by the Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Spend the drizzly hours 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 Detroit | Detroit Metropolitan Wayne County (DTW) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 8h 38m (1 stop) |
| Distance | 237 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $716 |
| Hotel, 2 nights (La Quinta Inn & Suites by Wyndham Chicago Downtown) | $842 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,078 |
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: Detroit to Chicago
| Per person | |
|---|---|
| This trip | $358 per person |
| Lowest in the last 30 days | $358 (Oct 13, 2026) |
| Typical price, last 60 days | $666 |
| Price checks | 6 |
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 for this domestic trip, and everything is priced in US dollars.
- The Frontier fare leaves DTW at 3:01 PM and lands at ORD at 10:39 PM, with 1 stop.
- Of the three hotels, only La Quinta Inn & Suites by Wyndham Chicago Downtown includes breakfast and free cancellation.
- Prices include taxes and fees as found when we checked, and they can change.
Questions readers ask
How much is the flight?
$358 per person round trip on Frontier, $716 for two, taxes and fees included when we checked. That's $308 below the typical fare on this route. A nonstop on American ran $511 per person.
Is it nonstop?
No. The Frontier fare has 1 stop and takes 8h 38m on Friday, Oct 16. American's nonstop takes 1h 34m, leaving at 1:35 PM and landing at 2:09 PM, for $511 per person.
What is the weather like?
Friday, Oct 16 shows drizzle, a high of 59°F and a 73% chance of rain. Saturday is overcast at 58°F with a 1% chance, and Sunday is overcast at 65°F with a 2% chance. Lows run 45°F to 49°F, so pack a jacket.
What does the whole weekend cost for two?
We estimate $2,078 for two: $716 in flights, $842 at La Quinta Inn & Suites by Wyndham Chicago Downtown and $520 for spending, which works out to $130 per person per day.
Is 2 nights enough?
For a first look, yes, even with the late Friday landing. Saturday covers a river cruise, Millennium Park and the Art Institute, and Sunday leaves time for deep-dish. Return flight times weren't in what we checked, so confirm them before you book.
Do I need a passport?
No. Chicago is in Illinois, you pay in US dollars, and clocks there run 1 hour behind Detroit.
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All trips from Detroit · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Image credits
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