Chicago from New Orleans, Oct 23–25: $1,366 for two, all in
The verdict
Our verdict
Worth it, if
- Fare is $21 below the typical fare on this route
- Hilton Chicago in The Loop, rated 7.9 from 983 reviews
- Highs of 58–75°F and rain chances of 12% to 25%
The catch: The $362 Frontier fare has one stop, takes 13h 47m and lands at 12:24 AM, and a checked bag is about $240 for two.
Worth it if you can give up Friday night to a long connection; skip it if you'd rather pay $1,002 for two on United's 2h 43m nonstop.
Worth it if you don't mind a long travel day: $1,366 for two, all in, covers Frontier flights at $724, Hilton Chicago at $554 and $88 in hotel fees, with taxes and fees included. The trip is Oct 23–25, 2026, for 2 nights. The flight isn't nonstop: it has one stop, takes 13h 47m and lands at 12:24 AM Saturday.
The total, before you go
$1,366 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $724 |
| Hilton Chicago, 2 nights, two guests, taxes in | $554 |
| Resort fee, collected at the desk | $88 |
| The total, before you go | $1,366 |
| A checked bag each, round trip (not in the total) | about $240 |
$21 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); 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
$362 per person, round trip
$724 for two, taxes and fees included · Frontier · 1 stop · 13h 47m
Out Fri, Oct 23, 10:37 AM – Sat, Oct 24, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $362 | 1 stop | 13h 47m |
| United | $501 | nonstop | 2h 43m |
| Frontier | $362 | 1 stop | 7h 1m |
Prices checked Oct 14, 2026, 5:22 PM CDT. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
The fare is $362 per person, $21 below the typical fare on this route of $383, and it carries the Lowest in 30 days badge. Across the 12 offers we checked, round-trip fares ran from $362 to $606 per person. That puts the whole weekend at $1,366 for two, covering the flights and the Hilton Chicago stay with taxes and the hotel's $88 in property fees. Late October looks mild for these dates: 63°F and overcast Friday, 75°F with a chance of drizzle Saturday and 58°F Sunday, with rain chances between 12% and 25%. It's a good weekend for walking The Loop, taking a river cruise and seeing a museum before the November holiday markets begin. We found these prices when we checked, and they can change before you book.
The kind of trip this is
This is a city weekend of architecture, museums, deep-dish and live blues at an easy pace, and most of it is walkable from The Loop or the Magnificent Mile. It suits a couple or two friends who like food and culture more than a packed schedule. It also suits people who don't mind starting Saturday after a late arrival the night before.
Weather in Chicago, Oct 23–25
Highs 58–75°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 63 °F | 59 °F | 12% |
| Sat, Oct 24 | 75 °F | 53 °F | 16% |
| Sun, Oct 25 | 58 °F | 49 °F | 25% |
Where to stay in Chicago
Hilton Chicago is the best-value pick and the hotel in the total. It's $554 for the 2 nights ($277 a night) plus $88 in fees at the property, and it scores 7.9 from 983 reviews. It sits in The Loop, with the architecture, theatres and Millennium Park at your doorstep. Sable At Navy Pier Chicago, Curio Collection By Hilton is the top rated at 8.9 from 887 reviews. It costs $769 for the stay plus $122 at the property and is on the Near North Side. Aloft by Marriott Chicago Mag Mile scores 8.1 from 2,534 reviews and costs $597 for the stay plus $95 at the property. It's in Streeterville, part of the Magnificent Mile / Streeterville area, which is handy for shopping on Michigan Avenue. None of the three offers free cancellation at these rates.
Hilton Chicago
$554 for 2 nights, two guests · $277 a night
See roomsSable At Navy Pier Chicago, Curio Collection By Hilton
$769 for 2 nights, two guests · $385 a night
See roomsAloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 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, a short walk from The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend Sunday morning 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 | 13h 47m (1 stop) |
| Distance | 836 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $724 |
| Hotel, 2 nights (Hilton Chicago) | $554 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,798 |
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 | $362 per person |
| Lowest in the last 30 days | $362 (Oct 14, 2026) |
| Typical price, last 60 days | $383 |
| Price checks | 14 |
Good to know
- Passport: no passport needed for travelers 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 there's no time difference from New Orleans.
- The Frontier flight goes from MSY to Chicago O'Hare (ORD), 836 miles, with one stop.
- A checked bag isn't in the total and runs about $240 for two.
- None of the three hotels offers free cancellation at the rates we found.
- The hotel total includes property fees: $88 at Hilton Chicago.
Questions readers ask
Is it worth it?
Yes, if a long travel day doesn't bother you. The fare is $21 below the typical fare on this route, but the outbound has one stop, takes 13h 47m and lands at 12:24 AM Saturday.
How much is the whole trip for two?
$1,366 for two, all in. That's $724 for Frontier flights, $554 for 2 nights at Hilton Chicago and $88 in hotel fees, taxes included. A checked bag, about $240 for two, and spending money are extra.
Is there a nonstop option?
Yes. United has a 2h 43m nonstop leaving at 7:00 AM and arriving at 9:43 AM, at $501 per person, or $1,002 for two, for the flights alone.
What is the weather like?
Mild for late October. Friday is 63°F and overcast, Saturday reaches 75°F with a chance of drizzle and Sunday is 58°F and overcast. Rain chances run from 12% to 25%.
Is 2 nights enough?
For a first look, yes. With a late Friday arrival, you'll realistically have Saturday and part of Sunday for a river cruise, Millennium Park, the Art Institute and a night of blues.
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