Chicago from Detroit, 23 – 25 Oct: £1,198 for two, all in
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The verdict
Our verdict
Worth it, if
- Fare is $84 per person below the typical fare on this route
- Top-rated hotel scores 8.8 from 775 reviews, with breakfast included
- Highs of 58–70°F with rain chances of 18% or less
The catch: Frontier's fare has one stop and takes 8h 38m to cover 237 miles, and a checked bag is about $240 for two.
Worth it if a lower fare matters more than a long Friday; skip it if you'd rather pay $1,062 for the 1h 40m nonstop.
Worth it if you don't mind a long travel day: $1,590 for two, all in, covers the Frontier flights at $902, 2 nights at Hilton Chicago at $594 and its $94 resort fee, taxes and fees included. You leave Friday, Oct 23 and come back Sunday, Oct 25, 2026. The fare isn't nonstop: it has one stop and takes 8h 38m, and checked bags and spending money aren't in the total.
The total, before you go
£1,198 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £680 |
| Hilton Chicago, 2 nights, two guests, taxes in | £448 |
| Resort fee, collected at the desk | £71 |
| The total, before you go | £1,198 |
| Hold luggage each, return (not in the total) | about £181 |
£63 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); 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
£340 per person, return
£680 for two, taxes and fees included · Frontier · 1 stop · 8h 38m
Out Fri, Oct 23, 3:01 PM – Fri, Oct 23, 10:39 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £340 | 1 stop | 8h 38m |
| American. Operated by SkyWest Airlines as American Eagle | £400 | nonstop | 1h 40m |
| F9 + LF | £393 | 2 stops | 31h 11m |
Prices checked 15 Oct 2026, 03:10 GMT-4. 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
The fare is $451 per person, $84 below the typical fare on this route, which is $535 across 9 earlier checks. The fares we saw this week ran from $451 to $531. Late October in Chicago looks mild enough for walking: highs of 70°F Friday, 64°F Saturday and 58°F Sunday, with rain chances between 13% and 18%, though Saturday and Sunday show drizzle. That's jacket weather for a river cruise and a museum day, and it comes before the November and December stretch of Christkindlmarket and holiday lights. The trade-off is time. The Frontier flight leaves Detroit at 3:01 PM and lands at O'Hare at 10:39 PM local time, so Friday goes to travel and the city really gets Saturday and Sunday. If the two of you want a big-city weekend of food, art and blues for a $1,590 total, it holds up.
The kind of trip this is
A city weekend built on food, architecture and live music, at an easy pace once you land. It suits a couple or two friends who'd rather walk between museums, pizza and a late blues set than lounge by a pool. Friday goes to getting there, so make Saturday the big day and keep Sunday loose for one more neighborhood before heading home.
Weather in Chicago, 23 – 25 Oct
Highs 58–70°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 70 °F | 56 °F | 13% |
| Sat 24 Oct | 64 °F | 58 °F | 18% |
| Sun 25 Oct | 58 °F | 49 °F | 15% |
Where to stay in Chicago
Hilton Chicago is the best-value pick and the one in the total: $594 for the 2 nights ($297 a night), a 7.9 review score from 982 reviews, room only. It's in The Loop, where the architecture, the theaters and Millennium Park are at your doorstep. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 775 reviews. It's $630 for the stay ($315 a night) with breakfast included, in the West Loop near the Randolph Street restaurant row. Aloft by Marriott Chicago Mag Mile is the budget pick at $597 ($299 a night), with a score of 8.1 from 2,534 reviews, in Streeterville close to the Michigan Avenue shops. None of the three offers free cancellation, and each one charges $94 to $100 in fees at the property.
Hilton Chicago
£448 for 2 nights, two guests · £224 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£475 for 2 nights, two guests · £237 a night
See roomsAloft by Marriott Chicago Mag Mile
£450 for 2 nights, two guests · £225 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 to see the skyline from the water
- See the Bean and the fountains in Millennium Park, at the doorstep of The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend drizzly Sunday morning inside 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
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 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 | £680 |
| Hotel, 2 nights (Hilton Chicago) | £448 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,520 |
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 | £340 per person |
| Lowest in the last 30 days | £270 (13 Oct 2026) |
| Typical price, last 60 days | £403 |
| Price checks | 9 |
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 1 hour behind Detroit, and the 10:39 PM arrival is in local time.
- Chicago has two airports, O'Hare (ORD) and Midway (MDW). This fare flies from DTW to ORD.
- None of the three hotels offers free cancellation, so settle your dates before you pay.
- The total covers the flights and the hotel with taxes and fees. A checked bag is about $240 for two, and we estimate $520 in spending money, for $2,016 overall.
Questions readers ask
Is it worth it?
Worth it if price matters more than time. The Frontier fare is $84 per person below the typical fare on this route, but it has one stop and takes 8h 38m. When we checked, a nonstop took 1h 40m and cost $531 per person.
How much is the whole trip for two?
$1,590, all in: $902 for the flights, plus $594 for 2 nights at Hilton Chicago and its $94 resort fee, with taxes and fees included. A checked bag is about $240 more for two, and we estimate $520 in spending money for the weekend.
Is there a nonstop?
Yes. When we checked, American (operated by SkyWest Airlines as American Eagle) had a nonstop leaving at 7:00 AM and landing at 7:40 AM local time. It takes 1h 40m and costs $531 per person, or $1,062 for two.
What is the weather like?
The forecast: Friday is overcast with a 70°F high and a 13% chance of rain. Saturday has drizzle, a 64°F high and an 18% chance. Sunday has drizzle, a 58°F high, a 49°F low and a 15% chance. Pack a light rain jacket.
Is 2 nights enough?
For a first visit, yes. The Frontier flight lands at 10:39 PM Friday, so you really get Saturday and Sunday. That's enough for the river cruise, Millennium Park, the Art Institute, deep-dish and a night of blues.
Do I need a passport?
No. Chicago is a domestic trip from Detroit, you pay in US dollars, and the clock goes back 1 hour.
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All trips from Detroit · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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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