Chicago from Houston, Oct 16–18: round trip from $372
A nonstop round trip from Houston (IAH) to Chicago (ORD) on F9 is $372 per person, or $744 for two, for Oct 16–18, 2026 (2 nights) when we checked. Highs run 52–62°F, and rain is most likely on Friday. The best-value hotel, Holiday Inn Chicago Midway Airport S by IHG, is $501 for the stay.
The flight
$391 $372 per person, round trip
the typical fare on this route
$744 for two, taxes and fees included · Frontier · nonstop · 5h 48m
Out Fri, Oct 16, 11:36 AM – Fri, Oct 16, 2:25 PM · back Sun, Oct 18, 7:40 AM – Sun, Oct 18, 10:39 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $372 | nonstop | 5h 48m |
| Frontier | $412 | 1 stop | 9h 23m |
| Frontier | $412 | 1 stop | 9h 40m |
Prices checked Oct 12, 2026, 7:18 PM 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 | $744 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $501 |
| Trip total for two | $1,245 |
Regular: $1,283 You pay: $1,245 Saved: $38
the typical fare on this route.
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Why go now
At $372 per person round trip and nonstop, this fare is $19 below the typical fare on this route. That's 5% under the $391 median from our earlier checks, and it's the lowest fare we've seen in 30 days. Across the 12 offers we checked, fares ran from $372 to $458. For two people, flights come to $744. Add the best-value hotel at $501 and $520 for spending, and the whole weekend comes to $1,765 for two. October is after the summer beach season and before the November holiday markets, so plan this as a city and food trip, not a lakefront one. The forecast has Friday at 56°F and overcast with a 60% chance of rain. Saturday is mostly clear at 52°F and Sunday is clear at 62°F. Pack a jacket and save the museums for Friday.
The kind of trip this is
This is a quick city getaway built around food, architecture and museums, with a blues club for Saturday night. It suits a couple or two friends who like to walk a lot, eat well and don't mind cool, jacket weather. The pace is brisk. You get Friday afternoon and evening plus one full day on Saturday, since the return flight leaves early Sunday morning.
Weather in Chicago, Oct 16–18
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 60% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best-value pick at $501 for the 2 nights ($251 a night). It's a 3-star Standard King Room rated 7.5 from 224 reviews. Heads-up: your flight lands at O'Hare, not Midway. River Hotel is the top-rated pick, with 4 stars and an 8.3 from 7,928 reviews, at $994 for the stay ($497 a night) for a Small Queen Room. Club Quarters Hotel Central Loop, Chicago is the budget pick of the two Loop hotels at $917 ($459 a night), rated 8.2 from 5,337 reviews. Both of those are in The Loop, where architecture, theatres and Millennium Park are at your doorstep. All three are room only, with no free cancellation.
Holiday Inn Chicago Midway Airport S by IHG
$501 for 2 nights, two guests · $251 a night
See roomsRiver Hotel
$994 for 2 nights, two guests · $497 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$917 for 2 nights, two guests · $459 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, when the forecast is mostly clear.
- See the Bean and the fountains in Millennium Park, right in The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's for Friday dinner.
- Spend Friday's overcast afternoon 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 Houston | George Bush Intercontinental (IAH), William P. Hobby (HOU) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 5h 48m nonstop |
| Distance | 942 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $744 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $501 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,765 |
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: Houston to Chicago
| Per person | |
|---|---|
| This trip | $372 per person |
| Lowest in the last 30 days | $372 (Oct 13, 2026) |
| Typical price, last 60 days | $391 |
| 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 Chicago is on the same time as Houston.
- The outbound flight leaves IAH at 11:36 AM on Friday, Oct 16 and lands at ORD at 2:25 PM. The return leaves at 7:40 AM on Sunday, Oct 18.
- The $372 fare is all-in, with taxes and fees included, as found when we checked. Prices can change before you book.
- All three hotels are room only, with no free cancellation, so be sure of your dates before you book.
- Chicago is 942 miles from Houston. Our spending budget uses $130 per person per day.
Questions readers ask
How much is the flight?
$372 per person round trip, nonstop on F9, or $744 for two, all-in when we checked. One-stop options on the same dates were $412 per person, so the nonstop is also the lower fare.
Do I need a passport?
No. Chicago is a domestic trip from Houston, you pay in US dollars and there's no time difference.
What is the weather like?
Friday is forecast at 56°F and overcast with a 60% chance of rain. Saturday is mostly clear at 52°F, with a low of 44°F. Sunday is clear at 62°F.
Is 2 nights enough?
It's tight but workable. You land at 2:25 PM on Friday and fly home at 7:40 AM on Sunday, so you get Friday evening plus all of Saturday. Staying in The Loop helps you fit in the river cruise, Millennium Park and the Art Institute.
What does the whole weekend cost for two?
$1,765 for two: $744 for flights, $501 for the best-value hotel and $520 for spending, as priced when we checked.
Which airports are we flying?
The nonstop fare goes from George Bush Intercontinental (IAH) to Chicago O'Hare International (ORD), both ways.
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Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
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