Chicago from Dallas-Fort Worth, Oct 23–25: round trip from $348
A round trip from Dallas-Fort Worth to Chicago costs $348 per person ($696 for two) for Oct 23–25, 2026. That's 2 nights, nonstop on Frontier from DFW to O'Hare. Expect highs of 59–68°F with a chance of showers, and the best-value hotel, Hilton Chicago in the Loop, is $522 for both nights.
The flight
$348 per person, round trip
$696 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 | $348 | nonstop | 5h 13m |
| LF | $359 | 1 stop | 19h 29m |
| Frontier | $348 | nonstop | 5h 17m |
Prices checked Oct 12, 2026, 1:26 AM CDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $696 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,218 |
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Why go now
The fare is $348 per person all-in, or $696 for two, for a nonstop round trip on Frontier. The median of our 6 earlier checks on this route is $363, so this fare is $15 below it, or 4% less. It's a modest dip, not a fire sale: the lowest we saw was $333 on Oct 12, and this one has no deal badge. The timing is what makes it worth a look. Late October brings highs of 59–68°F, cool enough to walk the Loop and the river all day. The trip also lands after the summer festivals and before the holiday markets, so the city keeps a normal pace. For a weekend of architecture, museums, deep-dish and blues, the numbers work. Prices were all-in when we checked and can change before you book.
The kind of trip this is
This is a city getaway built around food, culture and nightlife: skyscraper architecture, world-class museums, deep-dish pizza and blues clubs. It suits a couple or a pair of friends who like to walk and eat well. Expect a tight pace. You land after midnight, Saturday is your one full day, and the flight home leaves early Sunday morning. Plan one big day and a late night, not a slow wander.
Weather in Chicago, Oct 23–25
Highs 59–68°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 68 °F | 56 °F | 40% |
| Sat, Oct 24 | 59 °F | 52 °F | 29% |
| Sun, Oct 25 | 64 °F | 54 °F | 26% |
Where to stay in Chicago
Hilton Chicago is the best-value pick: $522 for the 2 nights ($261 a night) for a King Room, rated 7.9 from 981 reviews. It's room only, with no free cancellation. Hyatt Regency Chicago is the top-rated option at 8.6 from 1,478 reviews. It costs $901 for the stay ($451 a night) and is the only one of the three with free cancellation. Hampton Inn Chicago McCormick Place, the budget pick in the South Loop, is $548 ($274 a night). It's rated 8.5 from 735 reviews, and breakfast is included in a room with two queen beds. The Hilton and the Hyatt are both in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. That helps when Saturday is your only full day.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsHyatt Regency Chicago
$901 for 2 nights, two guests · $451 a night
See roomsHampton Inn Chicago McCormick Place
$548 for 2 nights, two guests · $274 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 to see the skyline from the water.
- See the Bean and the fountains in Millennium Park, an easy walk from The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's and settle the debate yourselves.
- Spend a few hours at the Art Institute of Chicago, a good plan if showers roll in.
- Hear live blues at Kingston Mines to close out Saturday night.
- Head to the West Loop for dinner along the restaurant row on Randolph Street.
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 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 | $696 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,738 |
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 | $348 per person |
| Lowest in the last 30 days | $333 (Oct 12, 2026) |
| Typical price, last 60 days | $363 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed. It's a domestic trip, you pay in US dollars and there's no time difference with Dallas.
- The outbound leaves DFW at 9:52 PM on Friday, Oct 23 and lands at O'Hare at 12:26 AM. The return leaves at 6:20 AM on Sunday, Oct 25.
- Weather: Friday 68°F with a 40% chance of showers, Saturday 59°F and overcast, Sunday 64°F with a 26% chance of showers.
- Hilton Chicago and Hampton Inn Chicago McCormick Place have no free cancellation. Hyatt Regency Chicago does.
- Our sample budget for two is $1,738: $696 for flights, $522 for the hotel and $520 for spending.
Questions readers ask
How much is the flight?
$348 per person round trip, or $696 for two, nonstop on Frontier from DFW to Chicago O'Hare. That price was all-in, taxes and fees included, when we checked. It's $15 under the $363 median of our earlier checks on this route. Fares move, so the live price may differ.
What are the flight times?
You leave DFW at 9:52 PM on Friday, Oct 23 and land at O'Hare at 12:26 AM Saturday. The return leaves at 6:20 AM on Sunday, Oct 25 and gets back at 8:59 AM. Both legs are nonstop.
Is 2 nights enough?
For one packed day, yes. With a past-midnight arrival and an early Sunday flight, Saturday is the whole trip. Pick a river cruise, the Art Institute, deep-dish and live blues, and you'll cover the highlights. If you want time to wander neighborhoods, this schedule is tight.
What's the weather like?
Cool and a little damp. Highs run 59–68°F and lows 52–56°F. Friday has a 40% chance of showers, Saturday is overcast at 59°F with a 29% chance of rain, and Sunday has a 26% chance of showers. Pack a layer and a rain jacket.
Do I need a passport?
No. It's a domestic flight from Dallas-Fort Worth to Chicago, 805 miles. You pay in US dollars and both cities are on the same time, so there's nothing to adjust.
Which hotel should we pick?
Go with Hilton Chicago in the Loop at $522 for 2 nights if price matters most. Choose Hyatt Regency Chicago at $901 if you want the 8.6 rating and free cancellation. The Hampton Inn Chicago McCormick Place at $548 includes breakfast.
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License