How does KAYAK find such low prices on flights from Oregon to Chicago Midway Airport?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oregon to Chicago Midway Airport.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oregon to Chicago Midway Airport?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Oregon is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Oregon to Chicago Midway Airport?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Oregon with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Chicago Midway Airport?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$150 CHEAP FLIGHTS from Oregon to Chicago Midway (MDW)

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

Cheap Flights from Oregon to Midway

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Oregon to Midway

Tue, Oct 20 - Sat, Oct 24

12:55 pm - 9:00 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 05m1 stop Denver Intl

5:10 am - 11:45 amMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

7h 35m1 stop Phoenix Sky Harbor Intl

$263Southwest

Tue, Oct 20 - Sat, Oct 24

12:55 pm - 9:00 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 05m1 stop Denver Intl

5:10 am - 11:45 amMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

7h 35m1 stop Phoenix Sky Harbor Intl

$263Southwest

Tue, Oct 20 - Sat, Oct 24

12:55 pm - 9:00 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 05m1 stop Denver Intl

6:35 am - 4:15 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

10h 40m2 stops Dallas Love Field Denver Intl

$269Southwest

Tue, Oct 20 - Sat, Oct 24

12:55 pm - 9:00 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 05m1 stop Denver Intl

6:35 am - 4:15 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

10h 40m2 stops Dallas Love Field Denver Intl

$269Southwest

Tue, Oct 20 - Sat, Oct 24

11:55 am - 9:00 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

8h 05m2 stops Phoenix Sky Harbor Intl Denver Intl

6:35 am - 4:15 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

10h 40m2 stops Dallas Love Field Denver Intl

$274Southwest

Tue, Oct 20 - Sat, Oct 24

11:55 am - 9:00 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

8h 05m2 stops Phoenix Sky Harbor Intl Denver Intl

6:35 am - 4:15 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

10h 40m2 stops Dallas Love Field Denver Intl

$274Southwest

Fri, Oct 16 - Tue, Oct 20

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

8:40 pm - 11:10 pmMDW Chicago Midway-PDX Portland

4h 30mnonstop

$322Southwest

Wed, Oct 14 - Wed, Oct 21

11:35 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 50mnonstop

12:15 pm - 8:10 pmMDW Chicago Midway-PDX Portland

9h 55m2 stops Austin Bergstrom Denver Intl

$329Southwest

Sat, Nov 7 - Wed, Nov 11

1:40 pm - 10:33 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 53m1 stop Atlanta Hartsfield-Jackson

5:29 pm - 11:56 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

7h 27m1 stop Minneapolis St Paul

$349Delta

Tue, Nov 3 - Thu, Nov 12

5:30 am - 11:47 amBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

5h 17m1 stop Minneapolis St Paul

6:00 am - 1:39 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

8h 39m1 stop Atlanta Hartsfield-Jackson

$349Delta

Recent last minute flight deals from Oregon to Midway

Wed, Sep 16 - Sat, Sep 19

11:30 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 55mnonstop

10:15 am - 12:30 pmMDW Chicago Midway-PDX Portland

4h 15mnonstop

$477Southwest

Sun, Sep 20 - Thu, Oct 1

5:51 pm - 9:07 amEUG Eugene-MDW Chicago Midway

13h 16m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

9:29 am - 5:11 pmMDW Chicago Midway-EUG Eugene

9h 42m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

$484Delta

Wed, Sep 16 - Sat, Sep 19

8:00 am - 5:05 pmPDX Portland-MDW Chicago Midway

7h 05m1 stop San Diego

6:00 pm - 8:20 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

$487Southwest

Sun, Sep 20 - Tue, Sep 22

11:30 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 55mnonstop

8:55 pm - 11:15 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

$492Southwest

Wed, Sep 16 - Sat, Sep 19

6:45 am - 4:05 pmPDX Portland-MDW Chicago Midway

7h 20m2 stops Denver Intl Des Moines

6:00 pm - 8:20 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

$492Southwest

Sat, Sep 19 - Wed, Sep 23

3:10 pm - 11:30 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 20m1 stop Las Vegas Harry Reid Intl

10:05 am - 2:50 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

5h 45m1 stop Denver Intl

$493Southwest

Sat, Sep 19 - Wed, Sep 23

3:10 pm - 11:30 pmBOI Boise Air Term. Gowen Fld-MDW Chicago Midway

7h 20m1 stop Las Vegas Harry Reid Intl

10:05 am - 2:50 pmMDW Chicago Midway-BOI Boise Air Term. Gowen Fld

5h 45m1 stop Denver Intl

$493Southwest

Fri, Sep 18 - Tue, Sep 22

12:25 am - 8:48 amPDX Portland-MDW Chicago Midway

6h 23m1 stop Minneapolis St Paul

1:00 pm - 6:59 pmMDW Chicago Midway-PDX Portland

7h 59m1 stop Atlanta Hartsfield-Jackson

$497Delta

Tue, Sep 15 - Wed, Sep 16

11:30 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 55mnonstop

8:55 pm - 11:15 pmMDW Chicago Midway-PDX Portland

4h 20mnonstop

$497Southwest

Wed, Sep 16 - Sat, Sep 19

11:30 pm - 5:25 amPDX Portland-MDW Chicago Midway

3h 55mnonstop

10:15 am - 12:30 pmMDW Chicago Midway-PDX Portland

4h 15mnonstop

$497Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$150

Best time to beat the crowds with an average 8% drop in price.

Most popular time to fly and prices are also 13% lower on average.

Flight from Portland to Chicago Midway Airport

How does KAYAK find such low prices on flights from Oregon to Chicago Midway Airport?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oregon to Chicago Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oregon to Chicago Midway Airport?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Oregon is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Oregon to Chicago Midway Airport?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Oregon with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Chicago Midway Airport?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

More options for your flight to Midway

Add a hotel or car rental

Airports

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

Complete your trip to Midway with a hotel stay or car rental

Car rentals in Chicago

MDW

$150 Find Cheap Flights from Oregon to Chicago Midway Airport - Compare and Save

Cheap Flights from Oregon to Midway

Recent round-trip flight deals from Oregon to Midway

Recent one-way flight deals from Oregon to Midway

Recent last minute flight deals from Oregon to Midway

Recent direct flight deals from Oregon to Midway

Good to know

Low season

High season

Cheapest flight

FAQs for booking Oregon to Chicago Midway Airport flights

Traveling to a place near Midway?

More options for your flight to Midway

Complete your trip to Midway with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights to Midway

Find direct flights for Midway

Flights from domestic origins to Oregon

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight