Destination: Chicago 2026

Starting this spring, travelers from the Willamette Valley have easy access to the Windy City, which is bursting with adventures for families.

By Donnita Bassinger, CTC, MCC

Chicago is one of those rare destinations where every season offers a completely different personality.

Winter brings a dusting of magic — yes, the snow can pile up, but so does the excitement. From the Christkindlmarket in Daley Plaza to indoor treasures like the Museum of Science and Industry’s Christmas Around the World exhibit, the city glows with warmth and light. Cozy up at new rooftop “winter lounges” with heated domes overlooking the skyline or catch a show at one of the city’s renowned theater houses in the Loop or on the North Side.

Spring brings the return of color to the city’s many parks and lakefront trails. The Chicago Riverwalk and Navy Pier buzz with energy, offering river cruises, live music and food festivals. By summer, the beaches along Lake Michigan come alive — and the newly expanded North Avenue Beach features floating cabanas and kayak rentals. It’s also festival season: the legendary Lollapalooza, Taste of Chicago, Chicago Blues Festival and the new Windy City Drone Light Show illuminate the sky from June through August.

Fall is ideal for sightseeing, with cooler air and thinner crowds. Architectural boat tours, the Open House Chicago design event, and the Art on the Mart digital projections keep visitors entertained

well past sunset.

For sports fans, Chicago reigns supreme. With six professional teams, it’s game time year-round — whether you’re cheering for the Cubs at Wrigley, the Bulls at the United Center or catching a Chicago Fire match at Soldier Field. Getting around is easier than ever thanks to the upgraded Ventra app from the Chicago Transit Authority which now integrates the public buses and trains with ride-sharing, bikes and CTA passes.

Smart sightseeing in 2026

Chicago remains a museum lover’s paradise, and sightseeing cards make it easier to see more for less. Chicago CityPASS® offers fast-track access to five world-class attractions — including the Shedd Aquarium, Skydeck Chicago, Field Museum, and your choice between the Adler Planetarium or Art Institute of Chicago. Prices start around $129 for adults and $99 for children (ages 3 to 11), valid for nine consecutive days.

New this year, visitors can use CityPASS mobile tickets directly on their phones — no paper, no waiting in line. Each pass includes timed-entry reservations to help you skip the long queues at popular spots like the Willis Tower Skydeck (complete with a new “Ledgewalk” harness experience added in 2023).

Go City: Chicago has expanded to over 35 attractions and tours — including the Museum of Illusions, 360 CHICAGO TILT Experience, Hop-On Hop-Off Big Bus Tour and Navy Pier’s Centennial Wheel. Three-day passes for up to seven total attractions start around $189 for adults and $134 for children. For a really fun experience, get the all-inclusive pass to visit as many attractions and tours as you can fit into three days for $229 per adult and $179 for children (age 3 to 12). It can be a fun challenge to map out your day to fit in as many attractions as possible. You get to experience things you would have never chosen to buy tickets to if you didn’t have the pass.

For families, Chicago’s new Kids Play Free summer initiative (available at select museums) can save even more. Meanwhile, the Lincoln Park Zoo — one of the last free zoos in the U.S. — just opened its Urban Wildlife Center, blending interactive tech exhibits with live habitats.

Chicago belongs on your travel list

Whether you visit for business, romance or a family getaway, Chicago offers something for everyone. The city features hotels from entry-level to luxury. For couples, rooftop dining at the LondonHouse or Gibsons Italia offers unforgettable sunset views. For families, new interactive exhibits at the Peggy Notebaert Nature Museum and Navy Pier’s Flyover Chicago 4D motion ride turn sightseeing into adventure.

From Oregon to Illinois, your next great escape is just one nonstop flight away. Book your trip, grab your CityPASS, and get ready to fall in love with the Windy City — now more vibrant, innovative and welcoming than ever.

New & exciting for 2026

Chicago keeps reinventing itself while staying true to its roots. In 2026, visitors can look forward to several new and buzzworthy attractions:

• Sears Tower Skywalk Expansion A new open-air deck 1,350 feet above the city with panoramic glass floors and augmented-reality skyline guides.

• The Obama Presidential Center (opening 2026 in Jackson Park) A stunning complex dedicated to civic engagement, culture and history, surrounded by new gardens and walking paths.

• Chicago River Eco-Walk A futuristic pedestrian trail that weaves through floating gardens, art installations and cafes along the riverbanks.

• Chicago Culinary Trail A self-guided food passport program launched by Choose Chicago that rewards travelers for visiting local favorites, from deep-dish pizza to new Michelin-rated vegan eateries.

• Smart Tourism Tech City Beacons now let you scan QR codes on lampposts for instant neighborhood guides, event calendars and transit tips in your language.

United Airlines is adding daily non-stop flights from Eugene Airport to Chicago O’Hare International Airport. O’Hare is a destination within itself, being named Best Airport in North America for over a decade. It features a sleek new Global Terminal with art exhibits, local restaurants and lush green

spaces between gates.

---

Meet Vacation MOM

Vacation MOM is brought to you in partnership with Eugene Airport

Donnita Basinger has been a travel agent for 40 years. She is the owner of VIP Vacations, Inc., and would be happy to chat with you about travel. She is a mom of three and lives in Eugene with her husband where she is active in Scouting and local charities.

Contact Donnita at 541-913-5272 or on facebook@VacationMOM