Cheap Flights To Chicago 2025

Chicago Flights as Low as $140

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.

Frontier Airlines
Fri, Aug 1 - Sun, Aug 3
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$140 Roundtrip, just found
$140
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 1 from Harry Reid Intl. to O'Hare Intl., returning Sun, Aug 3, priced at $140 just found
Spirit Airlines
Tue, May 13 - Tue, May 20
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 5 hours ago
$150
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, May 13 from Harry Reid Intl. to O'Hare Intl., returning Tue, May 20, priced at $150 found 5 hours ago
Spirit Airlines
Tue, May 13 - Wed, May 14
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, May 13 from Harry Reid Intl. to O'Hare Intl., returning Wed, May 14, priced at $160 found 5 hours ago
Frontier Airlines
Fri, Jun 20 - Sun, Jun 22
LAS
Harry Reid Intl.
MDW
Midway Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jun 20 from Harry Reid Intl. to Midway Intl., returning Sun, Jun 22, priced at $163 found 1 day ago
Spirit Airlines
Tue, Jun 10 - Tue, Jun 17
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 6 days ago
$164
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Jun 10 from Harry Reid Intl. to O'Hare Intl., returning Tue, Jun 17, priced at $164 found 6 days ago
Spirit Airlines
Fri, May 16 - Sun, May 18
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$165 Roundtrip, found 5 hours ago
$165
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Fri, May 16 from Harry Reid Intl. to O'Hare Intl., returning Sun, May 18, priced at $165 found 5 hours ago
Frontier Airlines
Mon, Jun 16 - Sun, Jun 22
LAS
Harry Reid Intl.
MDW
Midway Intl.
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jun 16 from Harry Reid Intl. to Midway Intl., returning Sun, Jun 22, priced at $168 found 1 day ago
Frontier Airlines
Sat, May 10 - Thu, May 15
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 10 from Hopkins Intl. to O'Hare Intl., returning Thu, May 15, priced at $180 found 5 days ago
Frontier Airlines
Sat, May 10 - Mon, May 12
CLE
Hopkins Intl.
MDW
Midway Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 10 from Hopkins Intl. to Midway Intl., returning Mon, May 12, priced at $191 found 1 day ago
United
Wed, Jul 30 - Mon, Aug 11
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$229 Roundtrip, found 3 hours ago
$229
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Jul 30 from Ronald Reagan Washington National to O'Hare Intl., returning Mon, Aug 11, priced at $229 found 3 hours ago
American Airlines
Wed, Jul 30 - Mon, Aug 11
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$229 Roundtrip, found 3 hours ago
$229
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Jul 30 from Ronald Reagan Washington National to O'Hare Intl., returning Mon, Aug 11, priced at $229 found 3 hours ago
Delta
Tue, Jun 17 - Tue, Jun 17
LAS
Harry Reid Intl.
MDW
Midway Intl.
$231 Roundtrip, found 1 day ago
$231
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 17 from Harry Reid Intl. to Midway Intl., returning Tue, Jun 17, priced at $231 found 1 day ago
Delta
Tue, Jul 29 - Fri, Aug 8
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$249 Roundtrip, found 3 hours ago
$249
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jul 29 from Ronald Reagan Washington National to Midway Intl., returning Fri, Aug 8, priced at $249 found 3 hours ago
Sun Country Airlines
Fri, May 16 - Sun, May 18
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$303 Roundtrip, found 5 hours ago
$303
Roundtrip
found 5 hours ago
Select Sun Country Airlines flight, departing Fri, May 16 from Harry Reid Intl. to O'Hare Intl., returning Sun, May 18, priced at $303 found 5 hours ago
JetBlue Airways
Mon, Aug 4 - Thu, Aug 7
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$312 Roundtrip, found 4 days ago
$312
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Aug 4 from Ronald Reagan Washington National to O'Hare Intl., returning Thu, Aug 7, priced at $312 found 4 days ago
Alaska Airlines
Thu, Jun 12 - Sun, Jun 15
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Thu, Jun 12 from Harry Reid Intl. to O'Hare Intl., returning Sun, Jun 15, priced at $377 found 6 days ago

Chicago 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 Chicago. AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. AARP Travel features members-only discounts with the best rates from Expedia, so members will get the best price in travel, guaranteed.

As an AARP member, you'll have the opportunity to take advantage of exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

Once you have got your trip scheduled, we'll show you a full list of deals for your route. Do not forget to look at flights to alternative airports nearby, which can help you find a lower fare.

Transportation at the Airport

Once you've reserved plane tickets to Chicago, you might want to book a rental car so you can get around on your own. You can request Chicago car rentals under our cars tab and get in the car as soon as you step out of the airport. For more information, check out the Chicago (and vicinity) Car Rentals Guide.

Chicago Activities

If you aren't sure where to start, we can help you with that as well. Not to worry—there's lots to do in this city. Chicago has so much to do, and we can help you get started.

If you're looking for some fun activities to do in Chicago, make sure you look at our "Things to Do in Chicago (and vicinity)" page for activities and excursions for the whole crew.

Where to Stay in Chicago

Chicago has hotel to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. Remember that you will get the best price out there when you stay with us.

Planning Your Trip to Chicago

Whether you are heading out on a business trip, exploring a place you have never been before or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. There is no better time than now to start booking your next trip. Book one of our flights today.