Chicago from Dallas-Fort Worth, Oct 16–18: $1,561 for two, all in
The verdict
Our verdict
Worth it, because
- Nonstop on Frontier, 2h 42m
- $28 per person below the typical fare on this route
- Club Quarters Hotel Central Loop, Chicago, rated 8.2 by 5,339 guests
The catch: A checked bag, seat picks and any resort fee are extra: they are not in the total.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Chicago from Dallas-Fort Worth is $334 per person round trip ($668 for two) for Oct 16–18, 2026, 2 nights, nonstop on Frontier in 2h 42m. Expect highs of 58–65°F, with drizzle likely Friday and dry, overcast skies after that. The best-value hotel, La Quinta Inn & Suites by Wyndham Chicago Downtown, is $842 for the stay with breakfast.
The total, before you go
$1,561 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $668 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | $893 |
| The total, before you go | $1,561 |
| A checked bag each, round trip (not in the total) | about $240 |
$28 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
$334 per person, round trip
$668 for two, taxes and fees included · Frontier · nonstop · 2h 42m
Out Fri, Oct 16, 4:14 PM – Fri, Oct 16, 6:56 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $334 | nonstop | 2h 42m |
| Frontier | $394 | 1 stop | 11h 36m |
| Frontier | $334 | nonstop | 2h 23m |
Prices checked Oct 14, 2026, 3:08 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
Tweak this trip
Why now
$334 per person, all-in, is $28 below the typical fare on this route. That's 8% under the $362 median of 15 earlier checks. We saw 12 fares for these dates, ranging from $334 to $456, and this one was the lowest. The flight is nonstop on Frontier. It leaves DFW at 4:14 PM on Friday, Oct 16 and lands at O'Hare at 6:56 PM, so you can work most of Friday and still have dinner in Chicago. In mid-October, highs run 58–65°F. Friday has an 82% chance of drizzle, and Saturday and Sunday look overcast with a 1% chance of rain. That's jacket weather, good for museums, a river cruise and deep-dish. We checked these prices at the time shown, and they can change before you book.
The kind of trip this is
This is a city weekend built around food, architecture and art, at an easy pace. Two nights gives you time for a museum, a river cruise, a deep-dish dinner and a late blues set without rushing. It suits a couple or a pair of friends who like walking between neighborhoods and don't need beach weather. Bring a jacket and a small umbrella for Friday.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 58 °F | 48 °F | 78% |
| Sat, Oct 17 | 58 °F | 45 °F | 7% |
| Sun, Oct 18 | 65 °F | 49 °F | 0% |
Where to stay in Chicago
La Quinta Inn & Suites by Wyndham Chicago Downtown is the best-value pick. It's in the Loop and costs $842 for 2 nights ($421 a night), with breakfast included and free cancellation. It has a review score of 8 from 3,744 reviews. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 776 reviews. It's $875 for the stay ($438 a night) with breakfast, but this rate can't be canceled for free. Hyatt Place Chicago/Downtown - The Loop is our budget pick at $854 ($427 a night), room only, with free cancellation and a score of 8.2 from 1,959 reviews. The Loop puts architecture, theatres and Millennium Park at your doorstep. The West Loop has converted warehouses and the restaurant row on Randolph Street.
Club Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 a night
See roomsHyatt Regency McCormick Place Chicago
$1,020 for 2 nights, two guests · $510 a night
See roomsCongress Plaza Hotel Chicago
$718 for 2 nights, two guests · $359 a night
See roomsAll hotels in Chicago for these dates
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
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 and see the skyline from the water.
- See the Bean and the fountains in Millennium Park, a short walk from the Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's. Friday's drizzle makes it a good pizza night.
- Spend an overcast Saturday 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 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 | 2h 42m nonstop |
| Distance | 805 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $668 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $893 |
| 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: Dallas-Fort Worth to Chicago
| Per person | |
|---|---|
| This trip | $334 per person |
| Lowest in the last 30 days | $333 (Oct 12, 2026) |
| Typical price, last 60 days | $362 |
| Price checks | 21 |
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).
- You don't need a passport. You'll pay in US dollars, and Chicago is on the same time as Dallas-Fort Worth.
- The flight covers 805 miles in 2h 42m nonstop, from DFW to Chicago O'Hare International (ORD).
- Prices are all-in, with taxes and fees, as we found them. They can change.
- La Quinta and Hyatt Place offer free cancellation. The Hampton Inn rate doesn't.
- Our rough budget for two is $2,030: $668 for flights, $842 for the hotel and $520 for spending ($130 per person per day).
Questions readers ask
How much is the flight?
$334 per person round trip, or $668 for two, all-in, nonstop on Frontier. The outbound flight leaves DFW at 4:14 PM on Friday, Oct 16 and lands at 6:56 PM. A later nonstop at 10:08 PM was the same price and lands at 12:31 AM. We didn't have return times, so check them on the airline's site.
Do I need a passport?
No. It's a domestic trip, you'll pay in US dollars, and there's no time difference from Dallas-Fort Worth.
What is the weather like?
Friday, Oct 16 looks like drizzle, with an 82% chance of rain and temperatures of 47–59°F. Saturday is overcast at 45–58°F, and Sunday is overcast at 49–65°F. Both weekend days have a 1% chance of rain.
Is 2 nights enough?
For a first look, yes. You land Friday at 6:56 PM, which leaves time for deep-dish that night. Saturday covers the river cruise, Millennium Park and the Art Institute, and you'll have Sunday morning before you head home.
What does the whole trip cost?
Our rough budget for two is $2,030: $668 for flights, $842 for La Quinta Inn & Suites by Wyndham Chicago Downtown and $520 for spending over 2 days.
Which hotel should I pick?
La Quinta is $842 with breakfast and free cancellation. Hampton Inn has the highest score at 8.8 and costs $875, but this rate isn't cancelable for free. Hyatt Place is $854, room only, with free cancellation.
Also found for you
The newest finds from Dallas-Fort Worth.
Just found · from Dallas-Fort WorthLowest in 30 daysWorth it, if
Honolulu & Oahu
Nov 14–23, 2026 · 9 nights
- $498 per person, $163 under the typical $661 fare
- Oasis Hotel Waikiki: 7.9 from 1,515 reviews, free cancellation
- Highs of 81–82°F and big-wave season on the North Shore
$2,662 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights $996 + hotel $1,439 + resort fee $227, taxes in · a checked bag each adds about $160
$163 per person below the typical fare on this route
United · with a stop · 11h 8m
The catch: The flight stops once and takes 11h 8m, the normals show drizzle most days, and a checked bag is about $160 for two extra.
Worth it if you want nine warm days in Waikiki at a low fare; skip it if an 11h 8m one-stop flight is a dealbreaker.
Tweak this trip
Just found · from Dallas-Fort Worth33% below typicalWorth it, if
Los Angeles
Nov 14–21, 2026 · 7 nights
- The fare is $136 below the typical fare on this route
- Typical highs of 67–76°F, with clear skies the first three days
- Free cancellation at all three stays, starting at $63 a night
$1,512 for two · 7 nights · flights, hotel, taxes & fees
Flights $545 + hotel $967, taxes in · a checked bag each adds about $240
Frontier · with a stop · 10h 49m
The catch: The fare in the total has one stop, which adds up to 10h 49m of travel over both days, and resort fees and a checked bag aren't included.
Worth it if a week of mild weather, food and sights matters more than a fast flight; if you want the nonstop, skip this fare.
Tweak this trip
Just found · from Dallas-Fort WorthLowest in 30 daysWorth it, if
New Orleans
Oct 16–18, 2026 · 2 nights
- Lowest in 30 days on this route
- Holiday Inn New Orleans-Downtown Superdome by IHG, rated 8.5 by 2,285 guests
- Highs 74–87°F, little rain expected
$1,232 for two · 2 nights · flights, hotel, taxes & fees
Flights $800 + hotel $432, taxes in · a checked bag each adds about $240
Frontier · with a stop · 7h 32m
The catch: Not nonstop: a stop on the way, 7h 32m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Tweak this trip
More trips
The weekend after · from Dallas-Fort WorthLowest in 30 days
Nashville
Oct 23–25, 2026 · 2 nights
- 2h Frontier nonstop to BNA, Friday at 3:48 PM
- $360 per person, $24 below the typical fare on this route
- Highs 62–66°F, with rain chances of 9% to 16%
$1,125 for two · 2 nights · flights, hotel, taxes & fees
Flights $720 + hotel $405, taxes in · a checked bag each adds about $240
Frontier · nonstop · 2h
The catch: All three hotels are near the airport or Opryland, not downtown, and a checked bag and spending money aren't in the total.
Worth it if you want live music, hot chicken and a short nonstop; skip it if you need to sleep steps from Lower Broadway.
A week away · from Dallas-Fort Worth22% below typicalWorth it, if
Los Cabos
Nov 14–21, 2026 · 7 nights
- $423 per person, $120 below the typical fare on this route
- Lumina at Cardinal Cabo San Lucas: 9 from 588 reviews, free cancellation
- Typical highs of 82–87°F for a week of beach time
$1,522 for two · 7 nights · flights, hotel, taxes & fees
Flights $846 + hotel $676, taxes in · a checked bag each adds about $160
Volaris · with a stop · 11h 42m
The catch: It's one stop, not nonstop, with 11h 42m of listed flight time, and resort fees and a checked bag are not in the total.
Worth it if you want a warm, easygoing beach week for two at a fair fare; skip it if you need a nonstop or whale season.
Just found · from Dallas-Fort WorthLowest in 30 daysWorth it, if
Honolulu & Oahu
Nov 14–23, 2026 · 9 nights
- $498 per person, $163 under the typical $661 fare
- Oasis Hotel Waikiki: 7.9 from 1,515 reviews, free cancellation
- Highs of 81–82°F and big-wave season on the North Shore
$2,662 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
Flights $996 + hotel $1,439 + resort fee $227, taxes in · a checked bag each adds about $160
$163 per person below the typical fare on this route
United · with a stop · 11h 8m
The catch: The flight stops once and takes 11h 8m, the normals show drizzle most days, and a checked bag is about $160 for two extra.
Worth it if you want nine warm days in Waikiki at a low fare; skip it if an 11h 8m one-stop flight is a dealbreaker.
Just found · from Dallas-Fort Worth33% below typicalWorth it, if
Los Angeles
Nov 14–21, 2026 · 7 nights
- The fare is $136 below the typical fare on this route
- Typical highs of 67–76°F, with clear skies the first three days
- Free cancellation at all three stays, starting at $63 a night
$1,512 for two · 7 nights · flights, hotel, taxes & fees
Flights $545 + hotel $967, taxes in · a checked bag each adds about $240
Frontier · with a stop · 10h 49m
The catch: The fare in the total has one stop, which adds up to 10h 49m of travel over both days, and resort fees and a checked bag aren't included.
Worth it if a week of mild weather, food and sights matters more than a fast flight; if you want the nonstop, skip this fare.
Just found · from Dallas-Fort WorthLowest in 30 daysWorth it, if
New Orleans
Oct 16–18, 2026 · 2 nights
- Lowest in 30 days on this route
- Holiday Inn New Orleans-Downtown Superdome by IHG, rated 8.5 by 2,285 guests
- Highs 74–87°F, little rain expected
$1,232 for two · 2 nights · flights, hotel, taxes & fees
Flights $800 + hotel $432, taxes in · a checked bag each adds about $240
Frontier · with a stop · 7h 32m
The catch: Not nonstop: a stop on the way, 7h 32m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
All trips from Dallas-Fort Worth · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.
Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License