$170 Cheap flight deals from Jackson (JAN) to Chicago (CHI)
This Weekend's Flight Deals from Jackson to Chicago
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JAN
Evers Intl.
ORD
O'Hare Intl.
$575 Roundtrip, found 1 day ago
$575
Roundtrip
found 1 day ago
Airfares from $170 One Way, $351 Round Trip from Jackson to Chicago
Prices starting at $351 for return flights and $170 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JAN
Jackson
ORD
Chicago
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
JAN
Jackson
MDW
Chicago
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
JAN
Jackson
ORD
Chicago
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
JAN
Jackson
MDW
Chicago
$356 Roundtrip, found 3 days ago
$356
Roundtrip
found 3 days ago
JAN
Jackson
MDW
Chicago
$362 Roundtrip, found 3 days ago
$362
Roundtrip
found 3 days ago
Chicago economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Eurostars Magnificent Mile
9/10 Wonderful! (3,506 reviews)
Jun 27 - Jun 29
2 night stay
Jackson (JAN) to Chicago (ORD)
American Airlines • Non-stop roundtrip • Coach
Price was $860, price is now $725 per person
$725
per person
found 1 day ago
This property is a central location to just about everything. I was able to walk to majority of my destinations.
Reviewed on Mar 10, 2026
5.0-star property
Trump International Hotel & Tower Chicago
9.4/10 Exceptional! (1,851 reviews)
Jun 27 - Jun 29
2 night stay
Jackson (JAN) to Chicago (ORD)
American Airlines • Non-stop roundtrip • Coach
Price was $1,186, price is now $961 per person
$961
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
4.0-star property
Level Chicago – Old Town
9/10 Wonderful! (468 reviews)
Jun 27 - Jun 29
2 night stay
Jackson (JAN) to Chicago (ORD)
American Airlines • Non-stop roundtrip • Coach
Price was $938, price is now $766 per person
$766
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
More About Flying To Chicago from Jackson
Flights to Chicago
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Flights from Jackson
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Jackson Airports
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