Chicago from Dallas-Fort Worth, 23 – 25 Oct: £918 for two, all in
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The verdict
Our verdict
Worth it, if
- Frontier nonstop at $348 per person, $15 below the typical $363
- Hilton Chicago in The Loop: 7.9 from 981 reviews, $261 a night
- Highs of 59–68°F, good for the river cruise and Millennium Park
The catch: You land at 12:26 AM Saturday and fly home at 6:20 AM Sunday, and a checked bag is about $240 for two.
Worth it if you want one packed Saturday of architecture, art and deep-dish; skip it if you want a slow weekend or need checked bags.
Worth it if you can live with a tight schedule: $1,218 for two covers the Frontier flights at $696 plus 2 nights at the Hilton Chicago at $522, taxes and fees included. You fly nonstop from DFW to O'Hare on Friday, Oct 23 at 9:52 PM and fly home Sunday, Oct 25 at 6:20 AM, so Saturday is your big day. Checked bags, resort fees and spending money are not in that total.
The total, before you go
£918 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £525 |
| Hilton Chicago, 2 nights, two guests, taxes in | £393 |
| The total, before you go | £918 |
| Hold luggage each, return (not in the total) | about £181 |
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); 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
£262 per person, return
£525 for two, taxes and fees included · Frontier · nonstop · 5h 13m
Out Fri, Oct 23, 9:52 PM – Sat, Oct 24, 12:26 AM · back Sun, Oct 25, 6:20 AM – Sun, Oct 25, 8:59 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £262 | nonstop | 5h 13m |
| LF | £271 | 1 stop | 19h 29m |
| Frontier | £262 | nonstop | 5h 17m |
Prices checked 12 Oct 2026, 01:26 GMT-5. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $348 per person, this Frontier nonstop is $15 below the typical $363 we've seen on this route, about 4% under. Add 2 nights at the Hilton Chicago for $522 and the trip comes to $1,218 for two, taxes and fees included, before checked bags, resort fees and spending money. Late October brings highs of 59–68°F: Friday has a 40% chance of showers, Saturday is overcast at 59°F with a 29% chance of rain, and Sunday sits at 26%. That's jacket weather for the architecture river cruise, the Art Institute and a long deep-dish dinner. The flight times keep it tight, so plan Saturday well and treat this as a city sprint rather than a lazy weekend. These prices are what we found when we checked, and they can change.
The kind of trip this is
A city weekend built around architecture, art and food. It suits a couple or two friends who like to walk, eat well and don't mind a quick pace: a late Friday arrival, one full Saturday and an early Sunday flight. Think a river cruise in the morning, a museum in the afternoon, then deep-dish and live blues at night.
Weather in Chicago, 23 – 25 Oct
Highs 59–68°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 68 °F | 56 °F | 40% |
| Sat 24 Oct | 59 °F | 52 °F | 29% |
| Sun 25 Oct | 64 °F | 54 °F | 26% |
Where to stay in Chicago
Our best-value pick is the Hilton Chicago in The Loop, $522 for the stay ($261 a night) for a King Room, rated 7.9 from 981 reviews; it's the hotel in the total, with no free cancellation. For the top-rated stay, the Hyatt Regency Chicago, also in The Loop, is $901 ($451 a night), rated 8.6 from 1,478 reviews, with free cancellation. The Hampton Inn Chicago McCormick Place in the South Loop is $548 ($274 a night), rated 8.5 from 735 reviews, with breakfast included and a room with two queen beds, handy for two friends. The Loop puts architecture, theatres and Millennium Park at your doorstep, which matters on a weekend this short.
Hilton Chicago
£393 for 2 nights, two guests · £197 a night
See roomsHyatt Regency Chicago
£679 for 2 nights, two guests · £340 a night
See roomsHampton Inn Chicago McCormick Place
£413 for 2 nights, two guests · £207 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 morning
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago if the showers roll in
- 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 Dallas-Fort Worth | Dallas Fort Worth International (DFW), Dallas Love Field (DAL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 5h 13m nonstop |
| Distance | 805 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £525 |
| Hotel, 2 nights (Hilton Chicago) | £393 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,310 |
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: Dallas-Fort Worth to Chicago
| Per person | |
|---|---|
| This trip | £262 per person |
| Lowest in the last 30 days | £251 (12 Oct 2026) |
| Typical price, last 60 days | £274 |
| Price checks | 6 |
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.
- No time difference: Dallas-Fort Worth and Chicago are on the same clock.
- Outbound Friday, Oct 23 leaves DFW at 9:52 PM; the return leaves Sunday, Oct 25 at 6:20 AM and lands at 8:59 AM.
- Checked bags aren't in the fare; budget about $240 for two.
- The Hilton Chicago rate has no free cancellation; the Hyatt Regency Chicago rate does.
Questions readers ask
Is it worth it?
Worth it if you want a fast city weekend. The fare is $348 per person, $15 below the typical $363, and the flight is nonstop. The trade-off is the schedule: you land at 12:26 AM Saturday and leave at 6:20 AM Sunday.
How much is the whole trip for two?
$1,218 all in: $696 for both round-trip Frontier fares plus $522 for 2 nights at the Hilton Chicago, taxes and fees included. Checked bags, about $240 for two, resort fees and spending money come on top.
Do I need a passport?
No. Chicago is a domestic trip from Dallas-Fort Worth, you pay in US dollars and there's no time difference.
What is the weather like?
Highs of 59–68°F. Friday has a 40% chance of showers, Saturday is overcast at 59°F with a 29% chance of rain, and Sunday is at 26%. Pack a jacket and an umbrella.
Is 2 nights enough?
For a sprint, yes. With a late Friday arrival and an early Sunday flight, Saturday is your full day: a river cruise, the Art Institute, deep-dish and blues all fit if you plan ahead.
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All trips from Dallas-Fort Worth · 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: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License