Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap flights from Jacksonville (JAX) to Chicago (CHI)

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Lowest round trip fares by airline from Jacksonville and Chicago

Cheapest prices ($53 One Way, $87 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 26
MCO
Orlando
ORD
Chicago
$53
Frontier Airlines
Fri, May 21
MCO
Orlando
ORD
Chicago
$57
Spirit Airlines
Tue, May 18
MCO
Orlando
ORD
Chicago
$59
American Airlines
Wed, May 19 - Tue, May 25
MCO
Orlando
ORD
Chicago
$87
Spirit Airlines
Wed, Oct 20
MCO
Orlando
MDW
Chicago
$89
Delta
Thu, May 20 - Tue, May 25
MCO
Orlando
ORD
Chicago
$91
American Airlines
Wed, May 19 - Tue, May 25
MCO
Orlando
ORD
Chicago
$106
Frontier Airlines
Sat, May 22
JAX
Jacksonville
ORD
Chicago
$117
JetBlue Airways
Sat, May 22 - Sat, May 22
MCO
Orlando
MDW
Chicago
$166
Bargain Flight
Thu, May 20 - Tue, May 25
JAX
Jacksonville
ORD
Chicago
$227
JetBlue Airways

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $94 per night from May 16 to May 16
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $79 per night from May 16 to May 16
Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...
3.1/5 (9 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $40 per night from May 16 to May 16
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 2021

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Flights Review

Dec 18, 2019

The flight from ORD was the best

A verified traveler
Jacksonville to Chicago · United

Fly From Jacksonville to Chicago

Origin Jacksonville
Destination Chicago
Number of Daily Flights 43
Earliest Flight Departure Date May 20
Latest Flight Departure Date May 21
Popular Airlines Spirit Airlines

Cheap flights from Jacksonville to Chicago

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a Chicago Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Chicago vacation that you can't get when you book flights and hotel separately.

Relax in Chicago With Confidence and Convenience

Going cheap doesn't mean giving up great service. Our agents are available 24/7 to help you find the right cheap flights and hotel, and to answer questions about your trip.

Need to grab a cheap travel deal while you're on the go? Download our mobile app, where you can search and book just like you would on your home computer. Stay in-the-know on great rates on flights from Jacksonville to Chicago by signing up for exclusive email deals.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.