Chicago from Houston, 16 – 18 Oct: £938 for two, all in
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The verdict
Our verdict
Worth it, if
- Nonstop IAH to O'Hare, leaving 11:36 AM and landing 2:25 PM
- $372 per person, $19 below the typical fare on this route
- Saturday mostly clear at 52°F, Sunday clear at 62°F
The catch: The $501 hotel is by Midway Airport, not downtown, Friday has a 60% rain chance, and a checked bag and resort fees aren't in the total.
Worth it if you want a low-cost city weekend and don't mind riding in to the sights; skip it if you want to walk out to the Loop.
Worth it if you don't mind staying out by Midway: $1,245 for two covers the nonstop round trip at $744 plus 2 nights at Holiday Inn Chicago Midway Airport S by IHG at $501, taxes and fees included. You fly nonstop on Frontier (F9) from IAH to O'Hare on Friday, Oct 16 at 11:36 AM and head home Sunday, Oct 18 at 7:40 AM.
The total, before you go
£938 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £561 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £378 |
| The total, before you go | £938 |
| Hold luggage each, return (not in the total) | about £181 |
£14 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); 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
£280 per person, return
£561 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 | £280 | nonstop | 5h 48m |
| Frontier | £311 | 1 stop | 9h 23m |
| Frontier | £311 | 1 stop | 9h 40m |
Prices checked 12 Oct 2026, 19:18 GMT-5. Prices change; the binding price is the one on the booking site.
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Why now
The nonstop fare is $372 per person. That's $19 below the typical fare on this route, a 5% gap, and the lowest we've found in 30 days. Across the 12 offers we checked, fares ran from $372 to $458 per person. Add the best-value hotel and the weekend comes to $1,245 for two, taxes and fees included. A checked bag, resort fees and spending money aren't in that number, and we'd set aside $520 for two to cover them. Pack a jacket for mid-October: Friday is overcast at 56°F with a 60% chance of rain, then Saturday is mostly clear at 52°F and Sunday is clear at 62°F. Houston and Chicago share a time zone, so you won't lose time to jet lag. This weekend is for architecture, museums and deep-dish.
The kind of trip this is
This is a quick city getaway built around food, architecture and culture, with blues clubs and nightlife once it gets dark. It suits a couple or two friends who like to walk a lot and pack a full Saturday. The pace is brisk: you land Friday afternoon and fly out early Sunday, so Saturday's clear sky is when you'll do most of your sightseeing.
Weather in Chicago, 16 – 18 Oct
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 56 °F | 46 °F | 60% |
| Sat 17 Oct | 52 °F | 44 °F | 1% |
| Sun 18 Oct | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is our best-value pick and the hotel in the total: $501 for 2 nights ($251 a night), 3 stars and a 7.5 from 224 reviews, in a Standard King Room. It's near Midway, so you'll be riding in to the sights. If you'd rather stay downtown, both of our other picks are in The Loop, close to the architecture, the theatres and Millennium Park. Club Quarters Hotel Central Loop, Chicago is the lower-priced Loop option at $917 for the stay ($459 a night), 4 stars and an 8.2 from 5,337 reviews. River Hotel is the top rated at $994 ($497 a night), 4 stars and an 8.3 from 7,928 reviews, in a Small Queen Room. All three are room only, and none has free cancellation.
Holiday Inn Chicago Midway Airport S by IHG
£378 for 2 nights, two guests · £189 a night
See roomsRiver Hotel
£749 for 2 nights, two guests · £375 a night
See roomsClub Quarters Hotel Central Loop, Chicago
£691 for 2 nights, two guests · £346 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 clear Saturday
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend rainy Friday 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 | £561 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £378 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,330 |
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 | £280 per person |
| Lowest in the last 30 days | £280 (13 Oct 2026) |
| Typical price, last 60 days | £295 |
| 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, you pay in US dollars and Houston and Chicago are on the same time.
- The flight covers 942 miles, with 5h 48m of flying time for the round trip.
- You fly into Chicago O'Hare International (ORD), but the best-value hotel is near Chicago Midway International (MDW).
- All three hotels are room only, and none of them offers free cancellation.
- Prices are all-in as we found them this week and can change before you book.
Questions readers ask
Is it worth it?
Yes, if you're fine staying near Midway. The fare is nonstop at $372 per person, $19 below the typical fare on this route, and it's the lowest we've seen in 30 days. If you want to stay downtown, the Loop hotels cost more, so the trip adds up to more.
How much is the whole trip for two?
It's $1,245 for two, taxes and fees included. That's $744 for the round-trip flights plus $501 for 2 nights at Holiday Inn Chicago Midway Airport S by IHG. A checked bag, resort fees and spending money aren't included. We'd plan on $520 for two in spending money.
What's the weather like?
It'll be cool. Friday, Oct 16 is overcast with a high of 56°F and a 60% chance of rain. Saturday is mostly clear at 52°F, and Sunday is clear at 62°F. Lows run 44°F to 46°F.
Is 2 nights enough?
It's enough for a tight weekend. You land at 2:25 PM Friday and your flight home leaves at 7:40 AM Sunday, so Saturday is your one full day. Plan the river cruise and Millennium Park for then.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars, and there's no time difference from Houston.
Can I cancel the hotel?
None of the three hotels we picked offers free cancellation, so make sure of your dates before you book. All three rates are room only.
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All trips from Houston · 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
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