What percentage of New Orleans to Chicago flights are direct?

Historically, a relatively small percentage of flights from New Orleans to Chicago are direct. Approximately 6.8% of flights on this route have been direct across the trailing 90 days. For flights that include stopovers, the median number of stopovers observed was 2. This indicates that travelers should anticipate connecting flights when planning their journey between these two cities.

How long does it take to fly from New Orleans to Chicago?

The direct flight time from New Orleans to Chicago typically averages 2 hours and 44 minutes, covering a distance of 1330 kilometers. For flights with one stop, the median duration historically extends to 8 hours and 28 minutes. This significant difference highlights the time-saving benefit of direct routes when available. Travelers should factor in these durations when planning their itinerary.

Should I set a price alert for New Orleans to Chicago flights?

Given that New Orleans to Chicago is classified as a regular deal route, setting a price alert is a beneficial strategy. This classification indicates that price fluctuations and deals occur with sufficient frequency to make alerts useful. Across the trailing 30 days, prices on this route have shown enough movement to warrant monitoring. An alert can help travelers capture a good price as it becomes available.

Flights From New Orleans

To Chicago

Cheap Flights from New Orleans to Chicago

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Deals from

New Orleans

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 4 days ago

476 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)

Today’s best flight deals from New Orleans to Chicago

Explore current cheapest deals departing from New Orleans to Chicago

2026-12-01 – 2026-12-08
MSY - Chicago
78% AI deal score
$275
$154
Round trip
2026-12-01 – 2026-12-15
MSY - Chicago
73% AI deal score
$239
$170
Round trip
2026-12-04 – 2026-12-08
MSY - Chicago
77% AI deal score
$292
$170
Round trip
2026-11-03 – 2026-11-14
MSY - Chicago
66% AI deal score
$223
$180
Round trip
2026-12-02 – 2026-12-07
MSY - Chicago
75% AI deal score
$286
$180
Round trip
2026-11-10 – 2026-11-11
MSY - Chicago
75% AI deal score
$287
$185
Round trip
2026-12-09 – 2026-12-15
MSY - Chicago
74% AI deal score
$282
$187
Round trip
2026-12-04 – 2026-12-15
MSY - Chicago
71% AI deal score
$245
$187
Round trip
2026-11-12 – 2026-11-15
MSY - Chicago
74% AI deal score
$286
$195
Round trip
2026-11-26 – 2026-12-14
MSY - Chicago
49% AI deal score
$226
$197
Round trip

New Orleans to Chicago: Overview

Insights for flights from New Orleans to Chicago

Only 3% of recent fares for flights from New Orleans to Chicago were classified as a good price. Right now, fares to Chicago are below the typical level, with prices typically ranging from $363–$728 and a median of $504. New deals for this route show up several times a week, offering opportunities to find competitive prices.

When looking for cheap flights from New Orleans to Chicago, the data indicates that January is typically the most affordable month to fly, with a median fare of $287. Following closely, February also offers lower prices, with a median of $351. March presents another favorable option, with a median fare of $443.

A typical journey from New Orleans to Chicago takes about 2h 44m. However, most itineraries on this route connect at least once, with connecting flights having a median duration of 27h 41m. Only 6.8% of recent fares were for direct flights from New Orleans to Chicago, meaning you will likely encounter one or more stops; connecting itineraries typically involve 2 stopovers.

The distance between New Orleans and Chicago is 1330 km, classifying this as a short-haul route. This means you can expect a relatively quick journey, even with potential connections.

How much is a round trip from New Orleans to Chicago

Regular price: $230 - $392

Prices for flights from New Orleans to Chicago are currently below the regular range.

The regular price range for flights from New Orleans to Chicago is between $230 and $392. The current lowest deal is $180 with Frontier Airlines, for travel from Dec 2 to Dec 7.

now $180

Low $230

High $392

The cheapest time to fly from New Orleans to Chicago

The cheapest month to fly from MSY to CHI is January, with a median price of $287. The most expensive month is March, with a median price of $764. Prices are generally lower from January to November.

January

Cheapest

Flights from $287

March

Most Expensive

Flights from $764

Jan

Feb

Mar

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from New Orleans to Chicago

United Airlines

Last-minute flights going from New Orleans to Chicago

Sun, Oct 11

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$601

$322

One-way

Wed, Oct 14

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$467

$293

One-way

Thu, Oct 15

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (MDW)

Frontier Airlines

$530

$351

One-way

Fri, Oct 16

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$513

$349

One-way

Fri, Oct 16

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$520

$351

One-way

Thu, Oct 22

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

United Airlines

$235

$342

One-way

Biggest price drops on these dates for flights from New Orleans to Chicago

2 nights

Oct 11 - Oct 13

$601 → $322

46%

2 nights

Oct 10 - Oct 12

$601 → $333

45%

1 night

Oct 11 - Oct 12

$603 → $362

40%

7 nights

Oct 14 - Oct 21

$467 → $293

37%

Popular Airports to fly from New Orleans to Chicago

New Orleans - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from MSY to CHI are below the typical level, with 3% good prices found.

📅 Best time to fly

January is historically cheapest at $287

Historically, January is the cheapest month to fly from MSY to CHI, with a median price of $287.

⏱️ Flight duration

Direct flights average 2h 44m

Direct flights from MSY to CHI typically take 2h 44m, while connecting flights average 27h 41m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant on this route, with a median of 2 stopovers when connecting.

🏆 Airline highlight

Frontier Airlines offers a deal at $180

Frontier Airlines recently offered a deal for $180 from MSY to CHI for Dec 2-Dec 7.

🎯 Booking tip

Deals are regular for this route

Deals for flights from MSY to CHI are regularly available within a 30-day window.

New Orleans main airports to depart from

Louis Armstrong New Orleans International (MSY)

Cheapest

Louis Armstrong New Orleans International Airport is a good choice for flights from New Orleans to Chicago.

📍 ~19 km from New Orleans city center (reachable by car)

💸 Flights from ~$145

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from New Orleans.

📍 ~25 km from Chicago city center (reachable by car, train, or bus).

💸 Flights from ~$144

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$254

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from New Orleans to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From MSY

Chicago, United States

75% AI deal score

$632

$521

Save $111

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from New Orleans to Chicago is typically 14-27 days before departure. During this period, the average price observed was $609. Booking within 0-6 days of departure generally saw average prices increase significantly to $1090. Even booking 60+ days out resulted in higher average prices of $676, indicating that planning within the recommended 14-27 day window can lead to better value.

Across the trailing quarter, a flight from New Orleans to Chicago is considered a good deal if it is priced at or below $363. The median price for this route historically has been $504. Prices above $728 typically fall into the higher end of the spectrum. By aiming for fares at or below the $363 threshold, travelers can confidently secure a favorable price for their journey.

Historically, the cheapest months to fly from New Orleans to Chicago are January and February. In January, the median price was $287, while February saw a median price of $351. March, with a median price of $443, was observed as the most expensive month across the trailing 270 days. The annual median price for this route is $504, suggesting that booking in early winter can offer significant savings.

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Flights to Chicago from other cities

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New Orleans to Chicago: Overview

Insights for flights from New Orleans to Chicago

The distance between New Orleans and Chicago is 1330 km, classifying this as a short-haul route. This means you can expect a relatively quick journey, even with potential connections.

How much is a round trip from New Orleans to Chicago

Regular price: $230 - $392

Prices for flights from New Orleans to Chicago are currently below the regular range.

The regular price range for flights from New Orleans to Chicago is between $230 and $392. The current lowest deal is $180 with Frontier Airlines, for travel from Dec 2 to Dec 7.

now $180

Low $230

High $392

The cheapest time to fly from New Orleans to Chicago

The cheapest month to fly from MSY to CHI is January, with a median price of $287. The most expensive month is March, with a median price of $764. Prices are generally lower from January to November.

January

Cheapest

Flights from $287

March

Most Expensive

Flights from $764

Jan

Feb

Mar

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from New Orleans to Chicago

United Airlines

Last-minute flights going from New Orleans to Chicago

Sun, Oct 11

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$601

$322

One-way

Wed, Oct 14

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$467

$293

One-way

Thu, Oct 15

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (MDW)

Frontier Airlines

$530

$351

One-way

Fri, Oct 16

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$513

$349

One-way

Fri, Oct 16

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

Frontier Airlines

$520

$351

One-way

Thu, Oct 22

⌛ Last-Minute

MSY - Chicago

New Orleans (MSY) - Chicago (ORD)

United Airlines

$235

$342

One-way

Biggest price drops on these dates for flights from New Orleans to Chicago

2 nights

Oct 11 - Oct 13

$601 → $322

46%

2 nights

Oct 10 - Oct 12

$601 → $333

45%

1 night

Oct 11 - Oct 12

$603 → $362

40%

7 nights

Oct 14 - Oct 21

$467 → $293

37%

Popular Airports to fly from New Orleans to Chicago