Chicago from Indianapolis, 23 – 25 Oct: £1,354 for two, all in
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The verdict
Our verdict
Worth it, because
- Nonstop on American. Operated by Republic Airways as American Eagle, 1h 25m
- £35 per person below the typical fare on this route
- Lowest in 30 days on this route
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
A round trip from Indianapolis to Chicago costs $637 per person ($1,274 for two) for Oct 23–25, 2026, 2 nights. You fly nonstop on American, operated by Republic Airways as American Eagle, in 1h 25m. Expect overcast skies with highs of 60–76°F and a small chance of rain, and the best-value hotel, Hilton Chicago, is $522 for the stay.
The total, before you go
£1,354 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £960 |
| Hilton Chicago, 2 nights, two guests, taxes in | £393 |
| The total, before you go | £1,354 |
| Hold luggage each, return (not in the total) | about £121 |
£35 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on American, £121 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
£480 per person, return
£960 for two, taxes and fees included · American. Operated by Republic Airways as American Eagle · nonstop · 1h 25m
Out Fri, Oct 23, 6:46 AM – Fri, Oct 23, 7:11 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American. Operated by Republic Airways as American Eagle | £480 | nonstop | 1h 25m |
| American. Operated by SkyWest Airlines as American Eagle | £480 | nonstop | 1h 28m |
| American. Operated by Republic Airways as American Eagle | £480 | nonstop | 1h 27m |
Prices checked 13 Oct 2026, 09:25 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
The fare is $637 per person round trip, or $1,274 for two. That's $47 below the typical fare on this route: in our earlier checks the fare was usually $684, so this one is 7% under. It also carries the Lowest in 30 days badge. In 9 checks this month, $637 was the lowest fare we saw, and the 12 offers we found ranged from $637 to $657. The flight is nonstop and takes 1h 25m. It leaves at 6:46 AM on Friday, Oct 23, and lands at 7:11 AM local time, so you get almost all of Friday in the city. The forecast is mild for late October: 76°F on Friday, then highs of 61°F and 60°F, with overcast skies and rain chances of 16% to 26%. That suits museums, a river cruise and deep-dish. Prices were all-in when we checked and can change.
The kind of trip this is
This is a city weekend built around architecture, museums, food and a night out, with the lakefront in the background. It suits a couple or two friends who like to walk a lot and eat well. You set the pace: the early Friday flight gets you three days in town on two nights, so you have time to fit in a cruise, a museum and a blues club without rushing.
Weather in Chicago, 23 – 25 Oct
Highs 60–76°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 76 °F | 62 °F | 26% |
| Sat 24 Oct | 61 °F | 52 °F | 25% |
| Sun 25 Oct | 60 °F | 52 °F | 16% |
Where to stay in Chicago
Hilton Chicago is the best value at $522 for 2 nights ($261 a night) for a King Room. It's a 3-star hotel rated 7.9 from 982 reviews, in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. Eurostars Magnificent Mile is the top-rated pick: 4 stars and 8.7 from 2,286 reviews, at $773 for the stay ($387 a night). It's in River North, the city's nightlife core, with galleries and steakhouses, and it's the only one of the three with free cancellation. Hilton Garden Inn Chicago Downtown South Loop is listed as the budget pick at $577 ($289 a night). It has 3 stars, a 7.9 from 482 reviews and is also in the Loop, but on these dates Hilton Chicago costs less. All three are room only.
Hilton Chicago
£393 for 2 nights, two guests · £197 a night
See roomsEurostars Magnificent Mile
£583 for 2 nights, two guests · £292 a night
See roomsHilton Garden Inn Chicago Downtown South Loop
£435 for 2 nights, two guests · £218 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, close to the Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's on your first night.
- Spend 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
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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 | 1h 25m nonstop |
| Distance | 165 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £960 |
| Hotel, 2 nights (Hilton Chicago) | £393 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,746 |
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 | £480 per person |
| Lowest in the last 30 days | £480 (13 Oct 2026) |
| Typical price, last 60 days | £516 |
| Price checks | 9 |
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: this is a domestic trip, and you pay in US dollars.
- Chicago is 1 hour behind Indianapolis, so the 6:46 AM flight lands at 7:11 AM local time.
- Flights land at Chicago O'Hare International (ORD). Chicago Midway International (MDW) also serves the city.
- Only Eurostars Magnificent Mile offers free cancellation. All three hotels are room only.
- Our rough budget for two: $1,274 for flights, $522 for the hotel and $520 for spending, which comes to $2,316.
Questions readers ask
How much is the flight?
It's $637 per person round trip, or $1,274 for two, nonstop on American, operated by Republic Airways as American Eagle. That's all-in with taxes and fees as we found it, and prices can change.
What departure times are there?
There are three nonstops on Friday, Oct 23, at 6:46 AM, 11:03 AM and 12:40 PM. Each is $637 per person, and flight times run from 1h 25m to 1h 28m.
Do I need a passport?
No. Chicago is a domestic trip, 165 miles from Indianapolis, and you pay in US dollars.
What is the weather like?
The forecast is overcast all three days. Highs are 76°F on Friday, 61°F on Saturday and 60°F on Sunday, with lows of 52–62°F. Rain chances are 26%, 25% and 16%.
Is 2 nights enough?
For a first look, yes. The 6:46 AM flight lands at 7:11 AM, so Friday is a full day. That leaves room for the river cruise, Millennium Park, the Art Institute, deep-dish and a blues night.
What does the whole weekend cost?
Our rough total for two is $2,316. That's $1,274 for flights, $522 for 2 nights at Hilton Chicago and $520 for spending.
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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
- Photo: Joshua Santos / Pexels, Pexels License