$98 Cheap flight deals from Jacksonville (JAX) to Rosemont (CHI)

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This Weekend's Flight Deals from Jacksonville to Rosemont

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.

Sat, Sep 12 - Sun, Sep 13
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$428 Roundtrip, found 1 day ago
$428
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Sun, Sep 13, priced at $428 found 1 day ago
Sun, Sep 13 - Tue, Sep 15
JAX
Jacksonville Intl.
MDW
Midway Intl.
$559 Roundtrip, found 8 hours ago
$559
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sun, Sep 13 from Jacksonville Intl. to Midway Intl., returning Tue, Sep 15, priced at $559 found 8 hours ago

Airfares from $98 One Way, $195 Round Trip from Jacksonville to Rosemont

Prices starting at $195 for return flights and $98 for one-way flights to Rosemont were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Nov 11 - Sat, Nov 14
JAX
Jacksonville
MDW
Chicago
$195 Roundtrip, found 11 hours ago
$195
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Jacksonville to Chicago, returning Sat, Nov 14, priced at $195 found 11 hours ago
Sat, Dec 5 - Tue, Dec 8
JAX
Jacksonville
ORD
Chicago
$225 Roundtrip, found 14 hours ago
$225
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Jacksonville to Chicago, returning Tue, Dec 8, priced at $225 found 14 hours ago
Sat, Oct 3 - Mon, Oct 5
JAX
Jacksonville
ORD
Chicago
$327 Roundtrip, found 5 hours ago
$327
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Oct 3 from Jacksonville to Chicago, returning Mon, Oct 5, priced at $327 found 5 hours ago
Sat, Oct 3 - Mon, Oct 5
JAX
Jacksonville
MDW
Chicago
$337 Roundtrip, found 5 hours ago
$337
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Oct 3 from Jacksonville to Chicago, returning Mon, Oct 5, priced at $337 found 5 hours ago
Wed, Sep 23 - Sat, Sep 26
JAX
Jacksonville
RFD
Rockford
$346 Roundtrip, found 6 days ago
$346
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 23 from Jacksonville to Rockford, returning Sat, Sep 26, priced at $346 found 6 days ago

Rosemont economy flight packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,512 reviews)

Oct 23 - Oct 25

2 night stay

Jacksonville (JAX) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $758, price is now $556 per person
$556
per person
found 1 day ago

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,174 reviews)

Oct 23 - Oct 25

2 night stay

Jacksonville (JAX) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $977, price is now $655 per person
$655
per person
found 1 day ago
Honestly did not meet expectations. Check in was very fast but overall staff was a cold and not friendly. The only exception were few members at the breakfast restaurant, Maitre D’ and a few of the Bussers. No one offered help with the bags when checking in or out. We were traveling with a toddler and stroller so our hands were pretty full. Everyone seemed very interested in just chatting with other staff members and not connecting with guests at the hotel. The rooftop seems to be adults only which was not mentioned after we asked reception about checking it out. We tried to go one day and they didn’t help get a high chair for our toddler. I even mentioned getting one from the second floor restaurant which they have and they said no. We ended up going somewhere else nearby instead. My son was not able to get a proper seat for his age. They pointed a a high top table which is absurd. The hotel has great potential and well located. Unfortunately needs more presence in the hospitality aspect which should be their number one priority. Also note that they charge a $250 fee at checking-in addition to the nightly rate deposit. They claim is for incidentals but is just a way to encourage you spend the money at the hotel restaurant or bar.

Reviewed on Sep 9, 2026

The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (165 reviews)

Nov 1 - Nov 4

3 night stay

Jacksonville (JAX) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $854, price is now $640 per person
$640
per person
found 24 hours ago
Old,

Reviewed on Sep 8, 2026

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More About Flying To Rosemont from Jacksonville

Route Information for Flights from Jacksonville to Rosemont

Origin Airport IATA Code
JAX
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Jacksonville to Rosemont

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.