Chicago from Little Rock, Oct 16–18: round trip from $484
Round-trip flights from Little Rock to Chicago were $484 per person ($968 for two) when we checked, for Friday, Oct 16 to Sunday, Oct 18, 2026, 2 nights. It's a nonstop on American, operated by Republic Airways as American Eagle, and the forecast shows highs of 52–62°F. The best-value hotel, Cambria Hotel Chicago Loop - Theatre District, comes to $882 for the stay.
The flight
$592 $484 per person, round trip
the typical fare on this route
$968 for two, taxes and fees included · American. Operated by Republic Airways as American Eagle · nonstop · 2h 7m
Out Fri, Oct 16, 7:53 PM – Fri, Oct 16, 10:00 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American. Operated by Republic Airways as American Eagle | $484 | nonstop | 2h 7m |
| Delta | $521 | 1 stop | 4h 50m |
| American. Operated by PSA Airlines as American Eagle | $521 | 1 stop | 5h 26m |
Prices checked Oct 12, 2026, 7:12 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 | $968 |
| Cambria Hotel Chicago Loop - Theatre District, 2 nights | $882 |
| Trip total for two | $1,850 |
Regular: $2,066 You pay: $1,850 Saved: $216
the typical fare on this route.
Tweak this trip
Why go now
At $484 per person all-in, this fare is $108 below the typical fare on this route. That typical figure is $592, the median of our earlier checks, so the fare carries the 18% below typical badge. We saw 12 offers ranging from $484 to $707 per person, and this was the only nonstop. It takes 2h 7m, leaving Little Rock at 7:53 PM Friday and landing at O'Hare at 10:00 PM. The one-stop options were $521 per person. It's mid-October, so expect fall weather. Saturday looks mostly clear with a high of 52°F and Sunday clear at 62°F. Friday is overcast with a 60% chance of rain, and you'll spend most of that evening in the air. It works well for a city weekend of museums, a river cruise and deep-dish. Prices are what we found when we checked and can change.
The kind of trip this is
This is a city weekend built around food, culture and a little nightlife. It suits a couple or two friends who like walking all day, eating well and fitting a museum, a boat tour and a blues club into two days. Saturday runs at a brisk pace and Sunday is easier, all in jacket weather from the low 50s to the low 60s.
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
All three picks are in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. Cambria Hotel Chicago Loop - Theatre District is the best value at $882 for 2 nights ($441 a night). That gets you a King Bed Non Smoking Room, rated 8.1 from 1,256 reviews, with free cancellation. River Hotel is the top rated at 8.3 from 7,928 reviews and costs $994 for the stay ($497 a night) for a Small Queen Room. Heads-up: it doesn't offer free cancellation. Congress Plaza Hotel Chicago is the budget pick at $750 ($375 a night) for a King Room, rated 7.1 from 4,548 reviews, with free cancellation. All three are 4-star and room only, so breakfast isn't included.
Cambria Hotel Chicago Loop - Theatre District
$882 for 2 nights, two guests · $441 a night
See roomsRiver Hotel
$994 for 2 nights, two guests · $497 a night
See roomsCongress Plaza Hotel Chicago
$750 for 2 nights, two guests · $375 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 for the skyline from the water.
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Spend Saturday morning at the Art Institute of Chicago.
- Hear live blues at Kingston Mines.
- Catch a Cubs game at Wrigley Field if one is on the schedule that weekend.
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Little Rock | Clinton National (LIT) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 7m nonstop |
| Distance | 554 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $968 |
| Hotel, 2 nights (Cambria Hotel Chicago Loop - Theatre District) | $882 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,370 |
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: Little Rock to Chicago
| Per person | |
|---|---|
| This trip | $484 per person |
| Lowest in the last 30 days | $429 (Oct 13, 2026) |
| Typical price, last 60 days | $592 |
| Price checks | 7 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, the currency is the US dollar, and Chicago is on the same time as Little Rock.
- The flight covers 554 miles in 2h 7m, from Clinton National (LIT) to Chicago O'Hare International (ORD).
- The fare is all-in, with taxes and fees included as of when we checked. Return flight times weren't in our check, so confirm them when you book.
- All three hotels are room only. Cambria and Congress Plaza offer free cancellation, but River Hotel doesn't.
- Our rough budget for two is $2,370: $968 in flights, $882 for the hotel and $520 for spending.
Questions readers ask
How much is the flight?
It's $484 per person round trip, or $968 for two, all-in when we checked. That's nonstop on American, operated by Republic Airways as American Eagle, and $108 below the typical fare on this route.
When does it leave?
It leaves Little Rock at 7:53 PM on Friday, Oct 16 and lands at O'Hare at 10:00 PM. The flight takes 2h 7m.
Do I need a passport?
No. It's a domestic trip, you'll pay in US dollars, and there's no time difference.
What is the weather like?
Friday is overcast, 56°F, with a 60% chance of rain. Saturday looks mostly clear with a high of 52°F, and Sunday is clear at 62°F. Lows run from 44°F to 46°F, so pack a jacket.
Is 2 nights enough?
For a first look, yes. With all three hotels in The Loop, Saturday can cover the river cruise, Millennium Park and the Art Institute, followed by deep-dish and blues at night.
What does the whole weekend cost for two?
We estimate $2,370 for two: $968 for flights, $882 at Cambria Hotel Chicago Loop - Theatre District and $520 for spending, which works out to $130 per person per day.
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
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- Photo: Mik Dominguez / Pexels, Pexels License