Used cars/Jeep Gladiator/Chicago

Used Jeep Gladiator in Chicago

112 used Jeep Gladiator are for sale at 67 dealers within 40 miles of downtown Chicago. The median price is $31,500 at 42,513 mi.

112For sale
$31,500Median price
42,513 miMedian mileage
31%Under market
67Dealers

Ranked among 109 used Jeep Gladiator

Best used Gladiator deals in Chicago

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Great deal #1 of 18

$31,500 $4,253 under market (11.9%) 2025 Jeep Gladiator Sport 4,912 mi · Used · Anvil Clearcoat Market price $35,753 · Score 92/100 At Dial Chevrolet

Great deal #2 of 22

$32,913 $4,243 under market (11.4%) 2022 Jeep Gladiator Mojave 24,811 mi · Used · Sarge Green Clearcoat Market price $37,156 · Score 90/100 At International Subaru - Orland Park

Great deal #4 of 22

$25,406 $5,905 under market (18.9%) 2022 Jeep Gladiator 50,764 mi · Used · Granite Crystal Metallic Clearcoat Market price $31,311 · Score 88/100 At Continental Toyota

Great deal #1 of 22

$23,995 $3,336 under market (12.2%) 2020 Jeep Gladiator Rubicon 86,298 mi · Used · Sting-Gray Market price $27,331 · Score 87/100 At AutoNation Hyundai O'Hare

Great deal #5 of 22

$30,500 $3,715 under market (10.9%) 2022 Jeep Gladiator Rubicon 42,649 mi · Used · Sarge Green Clearcoat Market price $34,215 · Score 86/100 At Dial Chevrolet

Great deal #8 of 22

$20,412 $2,602 under market (11.3%) 2022 Jeep Gladiator Sport 84,243 mi · Used · Bright White Clearcoat Market price $23,014 · Score 82/100 At Elgin Chrysler Dodge Jeep Ram

Good deal #2 of 22

$26,839 $1,689 under market (5.9%) 2020 Jeep Gladiator Overland 4x4 58,231 mi · Used · Silver Market price $28,528 · Score 72/100 At Advantage Chevrolet of Bolingbrook

Good deal #1 of 18

$30,378 $1,781 under market (5.5%) 2021 Jeep Gladiator Overland 4x4 37,995 mi · Used · Gray Market price $32,159 · Score 72/100 At Dralle Chevrolet Buick

Deals against the market

About 12% under market

The best-ranked used Jeep Gladiator in Chicago this week is at Dial Chevrolet. 31% of the 109 ranked cars here are advertised under market.

How a used car is ranked

Market price comes from every used Jeep Gladiator in Chicago: what price does at each year of age and each mile, then adjusted for trim, color and certified status. The score adds mileage for the car's age and whether the listing has photos. How we rank.

Prices by model year

Model years with at least 3 cars for sale. Advertised price is the dealer's own figure, before tax, title and registration. 1 of the 112 are certified pre-owned.
Model year	For sale	Median price	Median mileage
2026 Jeep Gladiator	5	$39,500	12,568 mi
2025 Jeep Gladiator	18	$36,636	15,108 mi
2024 Jeep Gladiator	10	$39,072	21,353 mi
2023 Jeep Gladiator	14	$32,312	30,922 mi
2022 Jeep Gladiator	23	$28,795	42,649 mi
2021 Jeep Gladiator	18	$27,801	67,609 mi
2020 Jeep Gladiator	24	$28,887	72,797 mi

Dealers with the most used Gladiator

All Chicago dealers

Quick answers

How many used Jeep Gladiator are for sale in Chicago?

112 used Jeep Gladiator, model years 2020 to 2026, are advertised by 67 dealers within 40 miles of downtown Chicago, as of November 13, 2026. 1 are certified pre-owned.

What does a used Jeep Gladiator cost in Chicago?

The median advertised price for a used Jeep Gladiator in Chicago is $31,500, from 109 advertised prices ranging from $18,994 to $50,368. Median mileage is 42,513 mi. Prices are before tax, title and registration.

Where is the best deal on a used Jeep Gladiator in Chicago?

The best-ranked used Jeep Gladiator in Chicago this week is at Dial Chevrolet, about 12% under market for its age and mileage. 31% of the 109 ranked cars are advertised at least 3% under market.

Which Chicago dealers have the most used Jeep Gladiator?

Zeigler Chrysler Dodge Jeep Ram of Downers Grove in Downers Grove (12), Dial Chevrolet in Chicago (4), James Chrysler Dodge Jeep Ram of Cedar Lake in Cedar Lake (4).

Carfinity reads each dealer's public website. A car listed on more than one site is counted once. Dealer sites in this summary were last read between November 3, 2026 and November 13, 2026.