Autumn in Chicago

Autumn brings brisk weather, parks filled with vibrantly colored leaves, and an endless array of pop-ups, markets and festive events. The residents of Optima Signature have easy access to all of the city’s most bewitching autumn pastimes. Here are a few of the many activities to do this autumn in Chicago. 

Chicago Classics

Chicago is home to many autumn events that are entirely unique to the city. Jack’s Pumpkin Pop-Up is one of them. The one-of-a-kind outdoor experience is home to an axe-throwing range, classic carnival games, a dense pumpkin patch and Chicago’s largest corn maze. Food trucks serving fall cuisine and bars serving seasonal cocktails can be found across the two-acre experience. General admission for Jack’s Pumpkin Pop-Up is $25 and it is open every day through October 31. You can find more information and get tickets here.

Just a few miles East of Jack’s Pumpkin Pop-Up, Navy Pier’s Pumpkin Lights transform the beloved spot into a must-do fall outing. Throughout the month, guests will find Pier-wide deals, festive activities and more than 1,000 decorated pumpkins. 

After finding carving inspiration at Navy Pier, an architectural boat or walking tour featuring Optima Signature is the perfect way to end a fall day. The crisp, breezy fall weather is perfect for a guided tour on foot through the heart of the city or down the Chicago River in one of its famous river cruises. The educational trips cover more than 50 of Chicago’s iconic buildings and are appreciated by tourists and city natives alike. You can learn more about Chicago’s renowned architecture tours here.  

Fall Day Trip

Just outside the city, you can find a handful of farms home to more traditional autumn favorites. Odyssey Fun Farm, located 40 minutes outside of the city in Tinley Park, is one of the many locations perfect for a fall day trip. The prized destination has zip lines, hayrides, a Pac-Man-themed corn maze and a full pumpkin patch. You can visit the farm every Thursday through Sunday from 10 a.m. to 6 p.m through Halloween.  

Apple picking makes for another fun fall activity. Located just outside of Libertyville, Heinz Orchard is Chicago’s closest. The small family-run orchard offers apple picking over other seasonal endeavors. Red and Golden Delicious, McIntosh, Empire and Jonathan apple trees all fill the spirited environment.  In addition to Heinz Orchard, you can find more apple orchards for the perfect day trip around Chicagoland here

Chicago’s autumn months don’t last long. So before time runs out, take advantage of the unique events located in the heart of Chicago, or plan a day trip to one of the many wonderful locations full of seasonal fun outside of the city.

Best Day Trips Close to the Chicago Area

Although Chicago is a huge city with plenty to explore, sometimes you just need a break from the bustle and noise. For our fellow Chicago residents who might need a weekend getaway this summer, here are the best day trips close to the Chicago area:

Indiana Dunes National Park. Credit: Paul J Everett on Flickr Creative Commons, CC BY 2.0 Deed

Indiana Dunes National Park

Chicago boasts some great beaches, but for something different, Indiana Dunes National Park is worth the drive over state borders. The park features over three miles of lakeshore lined with sand dunes, marshes, grasslands and forests. If you’re feeling adventurous, you can try their Three Dune Challenge and climb three of their tallest dunes in one day. 

Rockford, IL

Less than 100 miles northwest of Chicago, Rockford’s charm is just a quick road trip away. You can’t miss the Anderson Japanese Gardens, one of North America’s premiere Japanese gardens with over 12 acres of streams, waterfalls, koi-filled ponds and more. The Discovery Center Museum or the Burpee Museum of Natural History are great spots for kids and families to explore.

Milwaukee, WI

Whether you get there by car or Amtrak train, Milwaukee’s downtown has something for everyone. Murals and public art line the streets full of boutique shops, perfect for exploring without an agenda. Don’t miss the Milwaukee Art Museum, one of the city’s many museums, for the exhibits and the architecture of the building itself. Milwaukee is also a city for beer enthusiasts, with a few historic gems related to the Pabst Brewing Company.

Oak Park, IL

This one is right in Chicago’s suburbs, but we can’t skip over Oak Park’s ties to legendary architect Frank Lloyd Wright. His home and studio are in Oak Park, as are a series of other Prairie-style homes he designed. Take one of the many architectural tours dedicated to Wright’s work in the neighborhood.

Whether you’re exploring new museums, different scenery or a piece of architecture history, we hope this inspires you to find your new favorite getaway from the city!

Best Day Trips Close to the Phoenix/Scottsdale Area

Phoenix and Scottsdale, cities sitting shoulder to shoulder in Arizona, are the central and exciting location of several Optima communities, including Optima Biltmore Towers, Optima Sonoran Village, and Optima Camelview Village. And while Phoenix boasts being the vivacious capital of Arizona, and Scottsdale prides itself in being the locus of access and luxury, these two twin cities also share another benefit in common: their proximity to countless other exciting day trips and destinations in the state.

 To help inspire your next excursion, here are just a few of the best day trips close by: 

Grand Canyon

This is a destination that needs no introduction. The Grand Canyon is just under a two-and-a-half hour drive north out of Phoenix. That’s pretty easy access to one of the world’s premier tourist attractions — a site that attracts over 5 million visitors annually. With its layered bands of red rock revealing millions of years of geological history, there’s really no wrong way to enjoy this immense natural attraction, we recommend the South Rim and the Skywalk for the best view, as well as planning to hike, ride a mule, or whitewater raft for the adventurously inclined.  

Sedona, Arizona. Credit: Moonjazz on Flickr Creative Commons, CC BY-NC 2.0 Deed


A day trip to Sedona is well worth the two hour drive south from Phoenix. No doubt the drive down will be a sight to see, too — Sedona is surrounded by red-rock buttes, steep canyon walls and pine forests. The breathtaking landscape is the perfect setting for outdoor enthusiasts, who will enjoy the numerous trailheads across Red Rock State Park. Whether you’re into an intense ten-mile hike, or something more mild like birdwatching and picnicking, there’s something for everyone. Once you’ve gotten your fair share of the outdoors, take a trip into town to enjoy the vibrant arts scene, New Age shops, and countless spas.

Watson Lake, Prescott, Arizona. Credit: Photos by Clark on Flickr Creative Commons, CC BY-NC 2.0 Deed


Further proof of all there is to see just outside of Phoenix, Prescott isn’t even a two-hour trip away. There’s so much to do here that you may even end up wanting to stay more than a day. From the historic Whiskey Row downtown, perfect for bar hopping and catching a live music performance, to the many museums worth visiting, there’s an endless list of itinerary items within the city limits alone. And like everywhere else in Arizona, Prescott also boasts an outstanding roster of hiking and outdoor recreation on its perimeter, including Prescott National Forest and Watson Lake

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