Are direct flights from Memphis to Chicago always the best option?

Direct flights offer convenience and save time, but they are not always the cheapest option. Flights with layovers can sometimes be significantly more affordable, especially if you are willing to spend extra time traveling. Consider your priorities for cost versus travel duration.

Can flexible travel dates help on Memphis to Chicago flights?

Yes, being flexible with your travel dates can often lead to finding cheaper flights. Prices can vary greatly depending on the day of the week, time of year, and local events. Shifting your departure or return by a few days may result in notable savings.

What extra costs should I check before booking Memphis to Chicago flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Factor these into your total travel budget to avoid surprises.

Flights From Memphis

To Chicago

Cheap Flights from Memphis to Chicago

Browse current best options from Memphis. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Memphis

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 Memphis to Chicago

Explore current cheapest deals departing from Memphis to Chicago

2027-01-08 – 2027-01-25
MEM - Chicago
42% AI deal score
$197
$216
Round trip
2027-01-11 – 2027-01-25
MEM - Chicago
42% AI deal score
$208
$217
Round trip
2026-10-27 – 2026-10-31
MEM - Chicago
42% AI deal score
$153
$219
Round trip
2026-12-09 – 2026-12-12
MEM - Chicago
42% AI deal score
$142
$219
Round trip
2026-12-03 – 2026-12-06
MEM - Chicago
47% AI deal score
$265
$220
Round trip
2026-12-07 – 2026-12-10
MEM - Chicago
47% AI deal score
$267
$220
Round trip
2027-01-08 – 2027-01-21
MEM - Chicago
41% AI deal score
$203
$229
Round trip
2027-01-11 – 2027-01-21
MEM - Chicago
41% AI deal score
$211
$230
Round trip
2026-10-30 – 2026-11-12
MEM - Chicago
42% AI deal score
$218
$231
Round trip
2026-10-30 – 2026-10-31
MEM - Chicago
42% AI deal score
$145
$232
Round trip

Memphis to Chicago: Overview

Insights for flights from Memphis to Chicago

A typical journey from Memphis to Chicago, including connections, takes about 2h 6m. Given that most itineraries for this route involve at least one stop, this median duration reflects the overall travel experience rather than just the non-stop flight time. For connecting itineraries specifically, the median travel time extends to 26h 43m.

Right now, fares for cheap flights from Memphis to Chicago are typically between $340–$991, with a median of $651. Current fares are above the typical level for this route. Currently, 0% of recent fares are classified as a good price.

The cheapest time to fly from Memphis to Chicago is typically during the winter months. December and January both show a median fare of $227, making them the most affordable options. February also offers a median fare of $227, providing consistent value during this period.

Most itineraries for this route involve at least one connection, with 21.6% of recent fares being non-stop. When a connection is necessary, the typical number of stopovers is 2. This indicates that direct flights from Memphis to Chicago are less common, and travelers should account for potential layovers.

The distance between Memphis and Chicago is 774 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 Memphis to Chicago

Regular price: $224 - $457

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

The regular price range for flights from Memphis to Chicago is between $224 and $457. The current lowest deal is $217 with Breeze Airways for travel from Nov 6-Nov 12.

now $217

Low $224

High $457

The cheapest time to fly from Memphis to Chicago

The cheapest month to fly from Memphis to Chicago is January, with a median price of $227. The most expensive month is July, with a median price of $884. Prices are generally lower from January to December.

January

Cheapest

Flights from $227

July

Most Expensive

Flights from $884

Jan

Feb

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Memphis to Chicago

United Airlines

Last-minute flights going from Memphis to Chicago

Thu, Oct 8

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

Frontier Airlines

$459

$374

One-way

Tue, Oct 13

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

United Airlines

$152

$428

One-way

Thu, Oct 15

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

Frontier Airlines

$349

$387

One-way

Wed, Oct 21

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

United Airlines

$147

$429

One-way

Wed, Oct 21

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

United Airlines

$147

$429

One-way

Fri, Oct 23

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (MDW)

Alaska Airlines, Inc.

$160

$436

One-way

Biggest price drops on these dates for flights from Memphis to Chicago

2 nights

Oct 9 - Oct 11

$449 → $384

15%

3 nights

Nov 22 - Nov 25

$274 → $271

4 nights

Jan 31 - Feb 4

$247 → $248

3 nights

Nov 12 - Nov 15

$256 → $267

Popular Airports to fly from Memphis to Chicago

Memphis - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Memphis to Chicago are above the typical level, with a median price of $651.

📅 Best time to fly

Fly in December, January, or February for the best prices

Historically, the cheapest months to fly are December, January, and February, with a median of $227.

⏱️ Flight duration

Direct flights average 2h 6m

Direct flights from Memphis to Chicago typically take 2h 6m, while connecting flights average 26h 43m.

✈️ Airlines & availability

Connecting flights are more common

Only 21.6% of recent flights are direct, with connecting routes typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers offering direct flights on the Memphis to Chicago route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Memphis to Chicago appear regularly, typically within a 30-day window.

Memphis main airports to depart from

Memphis International (MEM)

Cheapest

Memphis International is a convenient option for flights from Memphis to Chicago.

📍 ~14 km from Memphis city center (reachable by car)

💸 Flights from ~$117

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient arrival option for flights from Memphis to Chicago.

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

💸 Flights from ~$117

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by car or Amtrak Hiawatha line)

💸 Flights from ~$311

Business & First Class Flight Deals to Chicago

47% AI deal score

$498

$487

Save $11

United Airlines

Business Class

From MEM

Elite

Dec 25

Chicago, United States

46% AI deal score

$484

$475

Save $9

United Airlines

Business Class

From MEM

Elite

Oct 30

Chicago, United States

46% AI deal score

$491

$489

Save $2

United Airlines

Business Class

From MEM

Elite

Nov 13

Chicago, United States

45% AI deal score

$475

United Airlines

Business Class

From MEM

Elite

Nov 07

Chicago, United States

45% AI deal score

$475

United Airlines

Business Class

From MEM

Elite

Nov 16

Chicago, United States

45% AI deal score

$487

United Airlines

Business Class

From MEM

Elite

Nov 22

Chicago, United States

45% AI deal score

$514

United Airlines

Business Class

From MEM

Elite

Oct 27

Chicago, United States

45% AI deal score

$518

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Finding affordable flights often involves comparing prices across different airlines and booking sites. Being flexible with your travel dates and considering flights on weekdays or during off-peak seasons may also help. Setting up price alerts can notify you when fares drop.

Booking in advance, often several weeks to a few months before your desired departure, can sometimes result in lower fares. However, prices can fluctuate, so monitoring trends may be beneficial. Last-minute bookings usually carry a higher cost.

Comparing nearby airports at both your origin and destination can sometimes uncover more affordable flight options. While it may add to your ground travel time, the potential savings on airfare can be significant. Always factor in the cost and convenience of transportation to and from alternative airports.

Related routes

More routes from Memphis

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Flights to Chicago from other cities

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Memphis to Chicago: Overview

Insights for flights from Memphis to Chicago

The distance between Memphis and Chicago is 774 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 Memphis to Chicago

Regular price: $224 - $457

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

The regular price range for flights from Memphis to Chicago is between $224 and $457. The current lowest deal is $217 with Breeze Airways for travel from Nov 6-Nov 12.

now $217

Low $224

High $457

The cheapest time to fly from Memphis to Chicago

January

Cheapest

Flights from $227

July

Most Expensive

Flights from $884

Jan

Feb

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Memphis to Chicago

United Airlines

Last-minute flights going from Memphis to Chicago

Thu, Oct 8

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

Frontier Airlines

$459

$374

One-way

Tue, Oct 13

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

United Airlines

$152

$428

One-way

Thu, Oct 15

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

Frontier Airlines

$349

$387

One-way

Wed, Oct 21

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

United Airlines

$147

$429

One-way

Wed, Oct 21

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (ORD)

United Airlines

$147

$429

One-way

Fri, Oct 23

⌛ Last-Minute

MEM - Chicago

Memphis (MEM) - Chicago (MDW)

Alaska Airlines, Inc.

$160

$436

One-way

Biggest price drops on these dates for flights from Memphis to Chicago

2 nights

Oct 9 - Oct 11

$449 → $384

15%

3 nights

Nov 22 - Nov 25

$274 → $271

4 nights

Jan 31 - Feb 4

$247 → $248

3 nights

Nov 12 - Nov 15

$256 → $267

Popular Airports to fly from Memphis to Chicago

Memphis - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Memphis to Chicago are above the typical level, with a median price of $651.

📅 Best time to fly

Fly in December, January, or February for the best prices

Historically, the cheapest months to fly are December, January, and February, with a median of $227.

⏱️ Flight duration

Direct flights average 2h 6m

Direct flights from Memphis to Chicago typically take 2h 6m, while connecting flights average 26h 43m.

✈️ Airlines & availability

Connecting flights are more common

Only 21.6% of recent flights are direct, with connecting routes typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers offering direct flights on the Memphis to Chicago route.

🎯 Booking tip

Deals appear regularly

Deals for flights from Memphis to Chicago appear regularly, typically within a 30-day window.

Memphis main airports to depart from

Memphis International (MEM)

Cheapest

Memphis International is a convenient option for flights from Memphis to Chicago.

📍 ~14 km from Memphis city center (reachable by car)

💸 Flights from ~$117

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient arrival option for flights from Memphis to Chicago.

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

💸 Flights from ~$117

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by car or Amtrak Hiawatha line)

💸 Flights from ~$311

Chicago, United States

47% AI deal score

$498

$487

Save $11

United Airlines

Business Class

From MEM

Elite

Dec 25

Chicago, United States

46% AI deal score

$484

$475

Save $9

United Airlines

Business Class

From MEM

Elite

Oct 30

Chicago, United States

46% AI deal score

$491

$489

Save $2

United Airlines

Business Class

From MEM

Elite

Nov 13

Chicago, United States

45% AI deal score

$475

United Airlines

Business Class

From MEM

Elite

Nov 07

Chicago, United States

45% AI deal score

$475

United Airlines

Business Class

From MEM

Elite

Nov 16

Chicago, United States

45% AI deal score

$487

United Airlines

Business Class

From MEM

Elite

Nov 22

Chicago, United States

45% AI deal score

$514

United Airlines

Business Class

From MEM

Elite

Oct 27

Chicago, United States

45% AI deal score

$518

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Memphis to Chicago

Today’s best flight deals from Memphis to Chicago

Memphis to Chicago: Overview

Insights for flights from Memphis to Chicago

How much is a round trip from Memphis to Chicago

The cheapest time to fly from Memphis to Chicago

Direct flights from Memphis to Chicago

Last-minute flights going from Memphis to Chicago

Biggest price drops on these dates for flights from Memphis to Chicago

Popular Airports to fly from Memphis to Chicago

Memphis - Chicago route insights

Recent fares are above the typical level

Fly in December, January, or February for the best prices

Direct flights average 2h 6m

Connecting flights are more common

United Airlines offers direct flights

Deals appear regularly

Memphis main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Jan 01

Jan 30

Oct 26

Oct 16

Oct 29

Dec 25

Oct 30

Nov 13

Nov 07

Nov 16

Nov 22

Oct 27

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Memphis to Chicago?

When should I book flights from Memphis to Chicago?

Should I compare nearby airports for flights from Memphis to Chicago?

Are direct flights from Memphis to Chicago always the best option?

Can flexible travel dates help on Memphis to Chicago flights?

What extra costs should I check before booking Memphis to Chicago flights?

Related routes

More routes from Memphis

Flights to Chicago from other cities

Memphis to Chicago: Overview

Insights for flights from Memphis to Chicago

How much is a round trip from Memphis to Chicago

The cheapest time to fly from Memphis to Chicago

Direct flights from Memphis to Chicago

Last-minute flights going from Memphis to Chicago

Biggest price drops on these dates for flights from Memphis to Chicago

Popular Airports to fly from Memphis to Chicago

Memphis - Chicago route insights

Recent fares are above the typical level

Fly in December, January, or February for the best prices

Direct flights average 2h 6m

Connecting flights are more common

United Airlines offers direct flights

Deals appear regularly

Memphis main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Jan 01

Jan 30

Oct 26

Oct 16

Oct 29

Dec 25

Oct 30

Nov 13

Nov 07

Nov 16

Nov 22

Oct 27

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Memphis to Chicago?

When should I book flights from Memphis to Chicago?

Should I compare nearby airports for flights from Memphis to Chicago?