Services
PriceProtect™
DriveShield™
GarageGuard™
Insurance
Car Insurance
Compare Car Insurance with Jerry
Jerry’s Expert Advice
Car Insurance Estimates
Home & Renters Insurance
Home Insurance
Renters Insurance
Loans
Car Loan
Compare Car Loans with Jerry
Jerry's Expert Advice
Car Loan Guides
Repairs
Car Repair Estimates
Repair Estimates for Popular Services
Advice
Read Car Content
Browse Jerry Car Advice
Check Out Expert Car QnA
Learn About How We Create Content
Jerry Data & Research
Recent Studies
Comprehensive Data Reports
Reviews
About
FAQ
MenuIcon
BACK

What's the best route from Portland to Chicago?

I’m keen to visit Chicago, but I want to save some money by driving rather than flying. I’m well aware that I’m in for quite a long road trip, but I want to map it out ahead of time. What’s the best way to get from Portland to Chicago?

avatar
Eric Schad · Updated on
Reviewed by Shannon Martin, Licensed Insurance Agent.
The journey from
Portland
 to
Chicago
 is certainly a lengthy one, crossing seven states and taking you from the West Coast to Lake Michigan. While you can take several routes depending on how much time you have, the best route from Portland to Chicago is as follows:
  • Hop on I-84 East until you reach
    Salt Lake City
  • Take exit 120A for I-80 East
  • Off I-80 East, take exit 4B for I-88 East just inside the Illinois state line near the Quad Cities
  • Interstate 88 will eventually merge into I-290, which will take you right into the heart of Chicago
The entire journey takes about 31 hours and covers a distance of 2,100 miles. Because of the length, you may want to split this trip up into three or four days or longer, depending on your fatigue level and if you want to make stops along the way.
Before you head out, adding
roadside assistance
 to your car insurance policy is a smart move in case you’re stranded. To compare rates quickly and easily, use the
Jerry
 app.
Jerry is a licensed insurance broker and insurance comparison tool that collects quotes from over 55 top-rated insurers in just 45 seconds. After you find a great rate, Jerry can help you buy new insurance and cancel your old policy. Users save an average of $800+ per year.
MORE:
How to join AAA and make sure you have roadside assistance
Driving TipsRoad SafetyTravel
View full answer 
Jerry user testimonial avatar
rating primary
“My experience with Jerry has been absolutely incredible. It took my car insurance from about $400/month to about $80. The entire experience is seamless.” - Gregory R.
Lower my car insurance too
WHY YOU CAN TRUST JERRY
Jerry partners with more than 50 insurance companies, but our content is independently researched, written, and fact-checked by our team of editors and agents. We aren’t paid for reviews or other content.

Join 4M+ members in lowering their car insurance

Find insurance savings

You Might Also Be Interested

card cover

The Best Road Trip from Chicago to Maine

Explore city life and the great outdoors as you wind through the midwest and into some of New England’s wonders on this Chicago to Maine road trip.
avatar
Tom Hindle
card cover

A Road Trip From Chicago to Seattle

We’ve compiled a great road trip from Chicago to Seattle, covering some of the best American towns, cities, and landmarks.
avatar
Michelle Ballestrasse
card cover

The Ultimate City Road Trip from New York City to Chicago

Take a road trip from New York City to Chicago, enjoying the sights (and foods!) in Philly, Pittsburgh, Cleveland along the way.
avatar
Melanie Reiff

Read Advice From Car Experts At Jerry

card cover

2020 Jeep Grand Cherokee Oil Capacity

The 2020 Jeep Grand Cherokee has a total oil capacity of exactly 6 quarts (roughly 5.7 liters) and requires synthetic 0W-20 motor oil. Click here to learn more.
avatar
Andrew Biro
card cover

A Guide to 1999 Cars

From superminis to outsized SUVs, these are the best 1999 cars.
avatar
R.E. Fulton
card cover

How to Find a 2009 Honda Pilot Radio Code

Look for your 2009 Honda Pilot radio code in your glove compartment or use your VIN and radio serial number. Here’s what to do.
avatar
David Ghanizadeh-Khoob

What Others Are Asking

How do I clean up my driving record in Louisiana?
I recently received my very first speeding ticket. A friend suggested that taking a defensive driving class could clear my driving record, but I don’t know if that’s true. How can I clean up my driving record in Louisiana?
avatar
Eric Schad
How much is a used 2016 Honda Accord?
I haven’t needed to look for a used car in a while. Have prices always been this high? How much is a used 2016 Honda Accord supposed to cost?
avatar
Drew Waterstreet
What is the difference between reckless driving and aggressive driving?
There are drivers with poor driving behaviors that will one day lead to an accident in my town. It’s gotten to the point where I will step up as a witness if our law enforcement wants to put a stop to this dangerous driving! Can you tell me the difference between reckless driving and aggressive driving so that I’ll be prepared?
avatar
Tiffany Leung
Browse All Questions

Browse More Content

Car Repair Resources

Insurance for Your Car

Insurance in Your State

    Insurance In Your City

    Easiest way to compare and buy car insurance

    √
    No long forms
    √
    No spam or unwanted phone calls
    √
    Quotes from top insurance companies
    Find insurance savings
    Car Insurance by Make
    Audi
    BMW
    Dodge
    Ford
    GMC
    Honda
    Hyundai
    Jeep
    Kia
    Lexus
    Mercedes-Benz
    Mitsubishi
    Subaru
    Tesla
    Toyota
    View all
    Car Insurance by Model
    Chevrolet Silverado
    Chevrolet Malibu
    Ford Escape
    GMC Sierra
    Honda Accord
    Honda Civic
    Hyundai Tucson
    Jeep Cherokee
    Jeep Wrangler
    Kia Forte
    Mazda 3
    Nissan Altima
    Subaru Outback
    Subaru Crosstrek
    Toyota Camry
    Toyota Corolla
    Toyota Tacoma
    Toyota Highlander
    Toyota Rav4
    Volkswagen Jetta
    View all
    Car Insurance by State
    AL
    AZ
    AR
    CA
    CO
    CT
    DE
    FL
    GA
    ID
    IL
    IN
    IA
    KS
    KY
    LA
    ME
    MD
    MA
    MI
    MN
    MS
    MO
    MT
    NE
    NV
    NH
    NJ
    NM
    NY
    NC
    ND
    OH
    OK
    OR
    PA
    RI
    SC
    SD
    TN
    TX
    UT
    VT
    VA
    WA
    WV
    WI
    WY
    Car Insurance by City
    Austin, TX
    Boston, MA
    Charlotte, NC
    Chicago, IL
    Columbus, OH
    Dallas, TX
    Denver, CO
    Houston, TX
    Indianapolis, IN
    Jacksonville, FL
    Las Vegas, NV
    Los Angeles, CA
    Nashville, TN
    New York, NY
    Philadelphia, PA
    Phoenix, AZ
    Portland, OR
    San Antonio, TX
    San Francisco, CA
    Seattle, WA
    View all
    Car Loan by Make
    Audi
    BMW
    Chevrolet
    Ford
    GMC
    Honda
    Hyundai
    Kia
    Lexus
    Nissan
    Mercedes-Benz
    Subaru
    Tesla
    Toyota
    View all
    Car Insurance by Company
    AAA
    Allstate
    Aspire Advantage
    Assurance America
    Bristol West
    Commonwealth
    Dairyland
    Encompass
    Infinity
    Kemper
    Mapfre
    Mercury
    National General
    Nationwide
    Plymouth Rock
    Progressive
    Safeco
    State Auto
    Travelers
    Car Loan by State
    AL
    AZ
    AR
    CA
    CO
    CT
    DE
    FL
    GA
    ID
    IL
    IN
    IA
    KS
    KY
    LA
    ME
    MD
    MA
    MI
    MN
    MS
    MO
    MT
    NE
    NV
    NH
    NJ
    NM
    NY
    NC
    ND
    OH
    OK
    OR
    PA
    RI
    SC
    SD
    TN
    TX
    UT
    VT
    VA
    WA
    WV
    WI
    WY
    Car Repair by Service
    AC Compressor Replacement Cost
    Battery Replacement Cost
    Fuel Injector Replacement Cost
    Fuel Pump Replacement Cost
    Ignition Coil Replacement Cost
    Oil Change Cost
    Oil Pan Replacement Cost
    Power Steering Fluid Service Cost
    Rotate Tires Cost
    Spark Plugs Replacement Cost
    Timing Belt Replacement Cost
    Valve Cover Gasket Replacement Cost
    Water Pump Replacement Cost
    Wheel Bearings Replacement Cost
    View all