Portland and Los Angeles with Leo/Drew

Portland and Los Angeles with Leo/Drew

Requiron Leo

Make it your trip
Fly
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Portland
— 4 nights
Fly
2
Los Angeles
— 5 nights
Fly

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Portland

— 4 nights

City of Roses

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Your day by day itinerary now includes Portland Center Stage at The Armory, Powell's City of Books and Room Escape Games. You'll find plenty of places to visit near Portland: Cannon Beach (Haystack Rock, Cannon Beach, &more). Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, stroll around Hoyt Arboretum, tour the pleasant surroundings at Forest Park, and admire the striking features of Pittock Mansion.

Before you visit Portland, use our trip planner to discover what you can do and see there.

Chicago to Portland is an approximately 7.5-hour flight. You can also drive; or take a train. The time zone difference moving from Central Standard Time (CST) to Pacific Standard Time (PST) is minus 2 hours. Traveling from Chicago in January, things will get a bit warmer in Portland: highs are around 46°F and lows about 35°F. Wrap up your sightseeing on the 5th (Tue) to allow time to travel to Los Angeles.

Things to do in Portland

Parks · Outdoors · Beaches · Nightlife

Side Trip

Los Angeles

— 5 nights

City of Angels

Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Explore Los Angeles' surroundings by going to Anaheim (Disney California Adventure Park & Downtown Disney District). Pack the 7th (Thu) with family-friendly diversions at Universal Studios Hollywood. There's much more to do: examine the collection at The Getty Center, catch a live performance at Walt Disney Concert Hall, look and learn at Griffith Observatory, and tour the pleasant surroundings at Venice Beach and Boardwalk.

To find where to stay, traveler tips, and other tourist information, you can read our Los Angeles trip itinerary planner.

You can fly from Portland to Los Angeles in 5 hours. Alternatively, you can drive; or take a bus. When traveling from Portland in January, plan for warmer days in Los Angeles, with highs around 70°F, while nights are a bit warmer with lows around 49°F. On the 10th (Sun), you'll have the morning to explore before heading back home.

Things to do in Los Angeles

Theme Parks · Museums · Beaches · Parks

Side Trips

Oregon travel guide

4.5
Gardens · State Parks · Specialty Museums
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.