Chicago from Indianapolis, 30 Oct – 1 Nov: £978 for two, all in
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The verdict
Our verdict
Not worth it this week
- Fare $372 per person, $310 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 982 reviews
- Highs of 51–56°F suit the Art Institute and the architecture river cruise
The catch: The F9 trip has a stop and takes 44h 57m in transit for a 165-mile hop, and a checked bag is about $240 for two.
Worth it if you can pay $509 per person for the American nonstop; skip this F9 fare if Monday morning is a workday.
Not worth it this week: the trip costs $1,298 for two, all in. That's $744 for the flights, $478 for Hilton Chicago and $76 in fees at the property, with taxes included. The 2 nights run Friday, Oct 30 to Sunday, Nov 1, 2026, on F9 with a stop, not nonstop, and the round trip takes 44h 57m in transit, so you land Saturday at 12:51 PM and get home Monday at 11:53 AM.
The total, before you go
£978 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £561 |
| Hilton Chicago, 2 nights, two guests, taxes in | £360 |
| Resort fee, collected at the desk | £57 |
| The total, before you go | £978 |
| Hold luggage each, return (not in the total) | about £181 |
£234 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); the resort fee is counted above. 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 · 1 stop · 44h 57m
Out Fri, Oct 30, 7:52 PM – Sat, Oct 31, 12:51 PM · back Sun, Nov 1, 7:55 AM – Mon, Nov 2, 11:53 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £280 | 1 stop | 44h 57m |
| American | £384 | nonstop | 1h 18m |
| F9 + B6 | £326 | 1 stop | 39h 17m |
Prices checked 15 Oct 2026, 02:06 GMT-4. 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
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Why now
At $372 per person, the fare is $310 below the typical fare on this route of $682, which is 45% less. It's also the lowest of the 12 offers we checked. The problem is the schedule. The F9 flight leaves Friday, Oct 30 at 7:52 PM and lands at O'Hare Saturday at 12:51 PM. The return leaves Sunday, Nov 1 at 7:55 AM and lands Monday, Nov 2 at 11:53 AM. That gives you one afternoon and one evening in Chicago, but you pay for 2 hotel nights. Expect late-fall city weather: typical highs of 51–56°F, overcast skies Friday and Saturday and drizzle on Sunday. If the low fare is what draws you, keep an eye on this route. If the city is what draws you, the American nonstop at $509 per person takes 1h 18m.
The kind of trip this is
This is a city weekend of architecture, museums, deep-dish pizza and live blues, made for two adults who like to walk a lot and eat well. With this schedule the pace is quick: one Saturday afternoon and one night. It suits a couple or two friends who pick a few things and let the rest go. Bring layers, because the low drops to 37°F on Sunday.
Weather in Chicago, 30 Oct – 1 Nov
Typical highs 51–56°F, lows near 41°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Fri 30 Oct | 56 °F | 46 °F | Overcast |
| Sat 31 Oct | 54 °F | 40 °F | Overcast |
| Sun 1 Nov | 51 °F | 37 °F | Drizzle |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Chicago
Hilton Chicago is the best-value pick and the one in the total. It's $478 for the 2 nights ($239 a night) plus $76 in fees at the property for a King Room, room only. It scores 7.9 from 982 reviews and sits in The Loop, with Millennium Park and the theaters at your doorstep. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 775 reviews. It's $530 for the stay with breakfast, plus $84 in fees at the property, and the West Loop puts you near the restaurant row on Randolph Street. Best Western Chicago Downtown-River North is the budget pick at $458 ($229 a night) plus $73 in fees, scoring 7.1 from 1,922 reviews. It's the only one of the three with free cancellation, and River North is good for galleries and nightlife.
Hilton Chicago
£360 for 2 nights, two guests · £180 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£399 for 2 nights, two guests · £200 a night
See roomsBest Western Chicago Downtown-River North
£345 for 2 nights, two guests · £173 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 afternoon after you land.
- See the Bean and the fountains in Millennium Park in The Loop.
- Spend a few hours at the Art Institute of Chicago, a good plan for overcast days.
- Eat deep-dish at Lou Malnati's or Pequod's for Saturday dinner.
- Hear live blues at Kingston Mines Saturday night, keeping the 7:55 AM Sunday flight in mind.
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 Indianapolis | Indianapolis International (IND) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 44h 57m (1 stop) |
| Distance | 165 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £561 |
| Hotel, 2 nights (Hilton Chicago) | £360 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,313 |
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: Indianapolis to Chicago
| Per person | |
|---|---|
| This trip | £280 per person |
| Lowest in the last 30 days | £276 (15 Oct 2026) |
| Typical price, last 60 days | £514 |
| Price checks | 14 |
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.
- Chicago is 1 hour behind Indianapolis, and the flight lands at Chicago O'Hare International (ORD).
- Prices are all in, taxes and fees included, as we found them when we checked; they can change.
- A checked bag is not in the total: it's about $240 for two.
- Hilton Chicago and the Hampton Inn don't offer free cancellation; the Best Western does.
Questions readers ask
Is it worth it?
Not this week. The fare is $372 per person, 45% below typical, but the F9 trip has a stop and takes 44h 57m in transit. You land Saturday at 12:51 PM and get home Monday, Nov 2 at 11:53 AM, so you pay for 2 hotel nights and sleep there one.
How much is the whole trip for two?
It's $1,298 all in: $744 for the flights, $478 for 2 nights at Hilton Chicago and $76 in fees at the property, taxes included. A checked bag, about $240 for two, and spending money aren't in it.
Is there a nonstop?
Yes. American has a nonstop at $509 per person. It leaves Friday, Oct 30 at 5:41 AM and lands at 5:59 AM Chicago time, a 1h 18m flight.
What is the weather like?
Typical highs are 51–56°F with lows near 41°F this time of year. Expect overcast skies Friday and Saturday and drizzle on Sunday, Nov 1, when the low drops to 37°F. These are seasonal normals, not a forecast.
Is 2 nights enough?
Two nights would be enough with a better schedule. On this fare you land Saturday at 12:51 PM and leave Sunday at 7:55 AM, so plan for the river cruise, deep-dish and one evening out.
Do I need a passport?
No. It's a domestic trip, prices are in US dollars, and Chicago is 1 hour behind Indianapolis.
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All trips from Indianapolis · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
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- Photo: Mik Dominguez / Pexels, Pexels License
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