Chicago from New Orleans, Oct 16–18: round trip from $379
Round-trip flights from New Orleans to Chicago are $379 per person ($758 for two) for Friday through Sunday, Oct 16–18, 2026, which is 2 nights. It's Frontier (F9) with 1 stop, and the forecast shows highs of 52–62°F with little rain after an overcast Friday. The best-value hotel, Cambria Hotel Chicago Loop - Theatre District, is $882 for the stay.
The flight
$379 per person, round trip
$758 for two, taxes and fees included · Frontier · 1 stop · 14h 2m
Out Fri, Oct 16, 5:25 PM – Sat, Oct 17, 12:31 AM · back Sun, Oct 18, 10:26 AM – Sun, Oct 18, 5:22 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $379 | 1 stop | 14h 2m |
| United | $627 | nonstop | 5h 14m |
| Frontier | $385 | 1 stop | 17h 16m |
Prices checked Oct 12, 2026, 11:11 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 | $758 |
| Cambria Hotel Chicago Loop - Theatre District, 2 nights | $882 |
| Trip total for two | $1,640 |
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Why go now
At $379 per person, this fare is $2 under the $381 median from our 9 earlier checks on this route, or 1% less. That's a fair price, not a steal. The lowest we saw was $362 on Oct 12, and it's gone now. For two people, flights ($758), the best-value hotel ($882) and $520 of spending money come to $2,160. That's an October city weekend with no passport and no time change. The forecast shows an overcast Friday at 56°F with a 56% chance of rain, then a mostly clear Saturday at 52°F and a clear Sunday at 62°F. Pack a jacket and plan to walk. It works for architecture, museums, deep-dish and blues. Prices are all-in as we found them and can change.
The kind of trip this is
A city break built on food and culture: skyscrapers from the river, a world-class art museum, deep-dish pizza and late blues sets. It suits couples or a pair of friends who like to walk a lot and eat well. You'll keep a quick pace, since you land after midnight Friday and fly home Sunday morning, so Saturday does most of the work.
Weather in Chicago, Oct 16–18
Highs 52–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 56% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Stay in The Loop, where architecture, theatres and Millennium Park are at your doorstep. Cambria Hotel Chicago Loop - Theatre District is the best value at $882 for 2 nights ($441 a night). It has a review score of 8.1 from 1,256 reviews, and you can cancel free. Club Quarters Hotel Central Loop, Chicago is $893 for the stay ($447 a night) and scores 8.2 from 5,337 reviews. It's the budget pick, but there's no free cancellation. Hyatt Regency McCormick Place Chicago in the South Loop is the top rated at 8.5 from 997 reviews. It costs $1,020 for the stay ($510 a night), comes with free cancellation and has a room with 1 queen and 1 double bed. If nightlife is the plan, look at River North instead.
Cambria Hotel Chicago Loop - Theatre District
$882 for 2 nights, two guests · $441 a night
See roomsHyatt Regency McCormick Place Chicago
$1,020 for 2 nights, two guests · $510 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 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 morning.
- 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 an 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 New Orleans | Louis Armstrong New Orleans International (MSY) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 14h 2m (1 stop) |
| Distance | 836 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $758 |
| Hotel, 2 nights (Cambria Hotel Chicago Loop - Theatre District) | $882 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,160 |
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: New Orleans to Chicago
| Per person | |
|---|---|
| This trip | $379 per person |
| Lowest in the last 30 days | $362 (Oct 12, 2026) |
| Typical price, last 60 days | $381 |
| Price checks | 9 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, you pay in US dollars and there's no time difference with New Orleans.
- The outbound leaves MSY at 5:25 PM Friday and reaches ORD at 12:31 AM Saturday, with 1 stop.
- The return leaves at 10:26 AM Sunday and lands at 5:22 PM. Total travel time is 14h 2m both ways.
- All three hotels are room only, and Club Quarters Hotel Central Loop, Chicago doesn't offer free cancellation.
- Our budget for two includes $130 a day for spending, which comes to $520.
Questions readers ask
How much is the flight?
It's $379 per person round trip, or $758 for two, on Frontier (F9) with 1 stop, all-in as we found it. A United nonstop was $627 per person. Prices can change.
What will the whole weekend cost for two?
We found $2,160 in total: $758 for flights, $882 for Cambria Hotel Chicago Loop - Theatre District and $520 for spending.
What is the weather like?
Friday looks overcast at 56°F with a 56% chance of rain. Saturday is mostly clear at 52°F and Sunday is clear at 62°F, with lows of 44–46°F.
Is 2 nights enough?
It's tight, since you land at 12:31 AM Saturday and fly out at 10:26 AM Sunday. Saturday is your full day, so pick the river cruise, the Art Institute, deep-dish and blues.
Do I need a passport?
No. It's a domestic trip of 836 miles, you pay in US dollars and Chicago is on the same time as New Orleans.
Is this a good price?
It's a fair one. At $379 it's $2 under the $381 median from our 9 earlier checks, or 1% less.
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License