$68 Cheap flight deals from Jacksonville (JAX) to Lincolnshire (CHI)

This Weekend's Flight Deals from Jacksonville to Lincolnshire

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.

Sun, Nov 1 - Mon, Nov 2
JAX
Jacksonville Intl.
MDW
Midway Intl.
$369 Roundtrip, found 4 days ago
$369
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Nov 1 from Jacksonville Intl. to Midway Intl., returning Mon, Nov 2, priced at $369 found 4 days ago
Sun, Nov 1 - Mon, Nov 2
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$471 Roundtrip, found 1 day ago
$471
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Nov 1 from Jacksonville Intl. to O'Hare Intl., returning Mon, Nov 2, priced at $471 found 1 day ago

Airfares from $68 One Way, $125 Round Trip from Jacksonville to Lincolnshire

Prices starting at $125 for return flights and $68 for one-way flights to Lincolnshire were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 14 - Mon, Nov 16
JAX
Jacksonville
MDW
Chicago
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Jacksonville to Chicago, returning Mon, Nov 16, priced at $125 found 5 days ago
Wed, Dec 2 - Wed, Dec 9
JAX
Jacksonville
ORD
Chicago
$135 Roundtrip, found 1 hour ago
$135
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Jacksonville to Chicago, returning Wed, Dec 9, priced at $135 found 1 hour ago
Sat, Dec 12 - Mon, Dec 14
JAX
Jacksonville
ORD
Chicago
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Dec 12 from Jacksonville to Chicago, returning Mon, Dec 14, priced at $220 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
JAX
Jacksonville
ORD
Chicago
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Nov 14 from Jacksonville to Chicago, returning Mon, Nov 16, priced at $257 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
JAX
Jacksonville
ORD
Chicago
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select United flight, departing Sat, Nov 14 from Jacksonville to Chicago, returning Mon, Nov 16, priced at $257 found 5 days ago

Lincolnshire economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
3.5-star property

Sports Illustrated Resorts Chicago

9/10 Wonderful! (1,527 reviews)

Dec 4 - Dec 7

3 night stay

Jacksonville (JAX) to Chicago (ORD)

United • Coach

Chicago (ORD) to Jacksonville (JAX)

Frontier Airlines • Coach
Price was $736, price is now $583 per person
$583
per person
found 1 day ago

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,555 reviews)

Dec 4 - Dec 7

3 night stay

Jacksonville (JAX) to Chicago (ORD)

United • Coach

Chicago (ORD) to Jacksonville (JAX)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,036, price is now $686 per person
$686
per person
found 1 day ago
Great location, nice rooms, nice rooftop bar and large breakfast buffet included.

Reviewed on Oct 28, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (591 reviews)

Dec 12 - Dec 17

5 night stay

Jacksonville (JAX) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $979, price is now $732 per person
$732
per person
found 1 day ago
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

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