Cheap Flights To Hillside 2025

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Hillside Flights as Low as $100

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Jul 16 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jul 16 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $100 found 2 days ago
Spirit Airlines
Wed, Aug 20 - Sun, Aug 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Aug 20 from Los Angeles Intl. to O'Hare Intl., returning Sun, Aug 24, priced at $130 found 3 days ago
Frontier Airlines
Sun, Jul 27 - Sun, Aug 3
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jul 27 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Aug 3, priced at $148 found 1 day ago
United
Tue, Jul 15 - Tue, Jul 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 15 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $155 found 2 days ago
American Airlines
Tue, Jul 15 - Tue, Jul 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 15 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $155 found 2 days ago
Frontier Airlines
Sat, Aug 2 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 6, priced at $168 found 1 day ago
Delta
Sat, Aug 2 - Sat, Aug 2
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 2 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $191 found 6 days ago
Delta
Tue, Jul 29 - Tue, Aug 5
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 29 from Love Field to Midway Intl., returning Tue, Aug 5, priced at $197 found 1 day ago
Delta
Sun, Jun 22 - Tue, Jun 24
BDL
Bradley Intl.
MDW
Midway Intl.
$197 Roundtrip, found 23 hours ago
$197
Roundtrip
found 23 hours ago
Select Delta flight, departing Sun, Jun 22 from Bradley Intl. to Midway Intl., returning Tue, Jun 24, priced at $197 found 23 hours ago
Delta
Sat, Aug 30 - Wed, Sep 3
DAL
Love Field
ORD
O'Hare Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 30 from Love Field to O'Hare Intl., returning Wed, Sep 3, priced at $197 found 3 days ago
Frontier Airlines
Mon, Jun 30 - Fri, Jul 4
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 6 days ago
$199
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Jun 30 from Sky Harbor Intl. to O'Hare Intl., returning Fri, Jul 4, priced at $199 found 6 days ago
Frontier Airlines
Sun, Sep 21 - Sat, Sep 27
BDL
Bradley Intl.
ORD
O'Hare Intl.
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Sep 21 from Bradley Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $214 found 6 days ago
Frontier Airlines
Sun, Jun 29 - Thu, Jul 10
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jun 29 from Sky Harbor Intl. to Midway Intl., returning Thu, Jul 10, priced at $218 found 1 day ago
Frontier Airlines
Tue, Aug 19 - Sat, Aug 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 19 from Los Angeles Intl. to Midway Intl., returning Sat, Aug 23, priced at $240 found 1 day ago
Alaska Airlines
Sat, Sep 20 - Mon, Sep 22
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$259 Roundtrip, found 6 days ago
$259
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Sep 20 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $259 found 6 days ago
Contour Airlines
Wed, Jul 30 - Mon, Aug 4
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Wed, Jul 30 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Aug 4, priced at $277 found 1 day ago

Flight Travel Guide

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to . AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. AARP Travel combines members-only discounts with the best rates from Expedia, offering members the best price in travel, guaranteed.

AARP members have the opportunity to take advantage of exclusive rates on:

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Whether it's a backpacking adventure, ski escape, weekend getaway, tropical destination or another trip you're dreaming of–we'll help you get there (without breaking the bank).

Airport Transportation

Once you have reserved plane tickets to , you might want to book a vehicle so you can get around the city. You can request a rental car under our cars tab and jump into the car as soon as you step out of the airport. For more information, check out the Hillside Car Rentals Guide.

Activities

Not sure where to start? Not to worry—there's so many things to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in , make sure you check out our "Things to Do in Hillside" page for excursions and activities for the whole crew.

Book Your Hotel in

has lodging to choose from, so you will have little difficulty finding a place to stay close to all the things you want to see. If you need to stay close to the airport, or another attraction in , check out our hotel listings page. No matter where you stay, just remember that you'll get the best price out there when you stay with us.

Booking Your Flight to

Once you have planned your travel dates, allow us here at AARP Travel to connect you with affordable tickets to . There is no better time than now to start booking your next trip. Book one of our flights today.