$38 Cheap flights from Oregon, IL

View $38 flight on Sun, Nov 8, 2026

Popular airlines from Oregon

Delta
American Airlines
United
Alaska Airlines
Frontier Airlines
JetBlue Airways
Air Canada

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Today's featured flight deals from Oregon

Nonstop

Carry-on included

Lower price than typical

Chicago (ORD) to San Juan (SJU).
Departing on Fri, Aug 28 at 5:20pm from Chicago, arriving at 11:15pm in San Juan.
Returning on Mon, Aug 31 at 8:55pm from San Juan, arriving on Tue, Sep 1 at 9:25am in Chicago.
American Airlines, nonstop.
60% less than typical

$302

Select American Airlines flight departing on Fri, Aug 28 at 5:20pm from Chicago, returning on Mon, Aug 31 at 8:55pm from San Juan priced at $302
Chicago (ORD) to San Juan (SJU).
Departing on Thu, Aug 27 at 5:20pm from Chicago, arriving at 11:15pm in San Juan.
Returning on Mon, Aug 31 at 8:55pm from San Juan, arriving on Tue, Sep 1 at 9:25am in Chicago.
American Airlines, nonstop.
60% less than typical

$302

Select American Airlines flight departing on Thu, Aug 27 at 5:20pm from Chicago, returning on Mon, Aug 31 at 8:55pm from San Juan priced at $302
Chicago (ORD) to San Juan (SJU).
Departing on Mon, Aug 24 at 5:20pm from Chicago, arriving at 11:15pm in San Juan.
Returning on Sat, Aug 29 at 12:55am from San Juan, arriving at 5:00am in Chicago.
American Airlines, nonstop.
65% less than typical

$282

Select American Airlines flight departing on Mon, Aug 24 at 5:20pm from Chicago, returning on Sat, Aug 29 at 12:55am from San Juan priced at $282

Chicago (ORD) to Orlando (MCO).
Departing on Thu, Sep 17 at 7:36pm from Chicago, arriving at 11:32pm in Orlando.
Returning on Mon, Sep 21 at 8:22am from Orlando, arriving at 10:29am in Chicago.
American Airlines, nonstop.
55% less than typical

$237

Select American Airlines flight departing on Thu, Sep 17 at 7:36pm from Chicago, returning on Mon, Sep 21 at 8:22am from Orlando priced at $237
Chicago (ORD) to Orlando (MCO).
Departing on Thu, Sep 10 at 7:36pm from Chicago, arriving at 11:32pm in Orlando.
Returning on Thu, Sep 17 at 8:23am from Orlando, arriving at 10:30am in Chicago.
American Airlines, nonstop.
50% less than typical

$237

Select American Airlines flight departing on Thu, Sep 10 at 7:36pm from Chicago, returning on Thu, Sep 17 at 8:23am from Orlando priced at $237
Chicago (ORD) to Orlando (MCO).
Departing on Fri, Sep 11 at 3:06pm from Chicago, arriving at 6:57pm in Orlando.
Returning on Wed, Sep 23 at 6:15am from Orlando, arriving at 8:29am in Chicago.
American Airlines, nonstop.
45% less than typical

$247

Select American Airlines flight departing on Fri, Sep 11 at 3:06pm from Chicago, returning on Wed, Sep 23 at 6:15am from Orlando priced at $247
Chicago (ORD) to Los Angeles (LAX).
Departing on Thu, Sep 3 at 6:00am from Chicago, arriving at 8:19am in Los Angeles.
Returning on Mon, Sep 7 at 7:35am from Los Angeles, arriving at 1:41pm in Chicago.
American Airlines, nonstop.
55% less than typical

$297

Select American Airlines flight departing on Thu, Sep 3 at 6:00am from Chicago, returning on Mon, Sep 7 at 7:35am from Los Angeles priced at $297
Chicago (ORD) to Los Angeles (LAX).
Departing on Thu, Sep 3 at 10:35pm from Chicago, arriving on Fri, Sep 4 at 12:58am in Los Angeles.
Returning on Mon, Sep 7 at 7:35am from Los Angeles, arriving at 1:41pm in Chicago.
American Airlines, nonstop.
55% less than typical

$297

Select American Airlines flight departing on Thu, Sep 3 at 10:35pm from Chicago, returning on Mon, Sep 7 at 7:35am from Los Angeles priced at $297
Chicago (ORD) to Los Angeles (LAX).
Departing on Wed, Sep 2 at 3:22pm from Chicago, arriving at 5:44pm in Los Angeles.
Returning on Mon, Sep 7 at 7:35am from Los Angeles, arriving at 1:41pm in Chicago.
American Airlines, nonstop.
55% less than typical

$307

Select American Airlines flight departing on Wed, Sep 2 at 3:22pm from Chicago, returning on Mon, Sep 7 at 7:35am from Los Angeles priced at $307
Chicago (ORD) to New York (JFK).
Departing on Sun, Sep 6 at 6:00am from Chicago, arriving at 9:24am in New York.
Returning on Sun, Sep 13 at 6:45am from New York, arriving at 1:45pm in Chicago.
Delta, nonstop.
50% less than typical

$265

Select Delta flight departing on Sun, Sep 6 at 6:00am from Chicago, returning on Sun, Sep 13 at 6:45am from New York priced at $265
Chicago (ORD) to New York (JFK).
Departing on Thu, Oct 1 at 10:59am from Chicago, arriving at 2:20pm in New York.
Returning on Sun, Oct 4 at 3:45pm from New York, arriving at 11:08pm in Chicago.
JetBlue Airways, nonstop.
45% less than typical

$260

Select JetBlue Airways flight departing on Thu, Oct 1 at 10:59am from Chicago, returning on Sun, Oct 4 at 3:45pm from New York priced at $260
Chicago (ORD) to New York (JFK).
Departing on Thu, Oct 1 at 1:35pm from Chicago, arriving at 5:00pm in New York.
Returning on Sun, Oct 4 at 3:45pm from New York, arriving at 11:08pm in Chicago.
American Airlines, nonstop.
45% less than typical

$260

Select American Airlines flight departing on Thu, Oct 1 at 1:35pm from Chicago, returning on Sun, Oct 4 at 3:45pm from New York priced at $260

Cheapest flights from Oregon

Prices were available within the past 7 days and start at $38 for one-way flights and $76 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

Sun, Oct 4 - Thu, Oct 8

RFD

Rockford

FLL

Fort Lauderdale

$76

Roundtrip

Found 3 hours ago

Tue, Sep 15 - Thu, Sep 17

ORD

Chicago

FLL

Fort Lauderdale

$82

Roundtrip

Just found

Mon, Aug 31 - Fri, Sep 11

RFD

Rockford

SFB

Orlando

$104

Roundtrip

Found 3 days ago

Sun, Nov 15 - Thu, Dec 3

RFD

Rockford

LAS

Las Vegas

$106

Roundtrip

Found 19 hours ago

Sat, Oct 3 - Wed, Oct 21

RFD

Rockford

AZA

Mesa

$123

Roundtrip

Found 2 days ago

Wed, Sep 9 - Sat, Sep 12

ORD

Chicago

MCO

Orlando

$136

Roundtrip

Just found

Mon, Aug 31 - Wed, Sep 2

RFD

Rockford

FLL

Fort Lauderdale

$139

Roundtrip

Found 6 days ago

Sat, Sep 5 - Sun, Sep 6

ORD

Chicago

ATL

Atlanta

$140

Roundtrip

Just found

Mon, Nov 2 - Mon, Nov 2

MDW

Chicago

FLL

Fort Lauderdale

$164

Roundtrip

Found 6 days ago

Sat, Oct 3 - Sat, Oct 10

ORD

Chicago

FLL

Fort Lauderdale

$171

Roundtrip

Just found

Travel information

Origin city name	Chicago
Origin airport	Chicago O'Hare Intl. Airport
Origin airport IATA code	ORD
Airlines serving	American Airlines, United, Delta, Alaska Airlines, JetBlue Airways, Frontier Airlines, Air Canada, Turkish Airlines, Lufthansa, Aeromexico, British Airways, Swiss International Air Lines, Volaris, Finnair, Emirates, Iberia, Viva Aerobus, Austrian Airlines, LOT-Polish Airlines, Brussels Airlines, SAS, Aer Lingus, Qatar Airways, Cathay Pacific, TAP Portugal, Etihad Airways, KLM, Japan Airlines, All Nippon Airways, Icelandair, Avianca, EVA Airways, Air France, Korean Air, Copa, IndiGo
Popular airline	American Airlines
Roundtrip price	$106

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$38 Cheap flights from Oregon, IL

Popular airlines from Oregon

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Today's featured flight deals from Oregon

Cheapest flights from Oregon

Travel information

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