4 Chicago North Shore Day-Trip Ideas

If you’ve ever felt like there’s just too much to do and see around Chicago’s North Shore, we understand! There is a lot to explore — and you don’t need to venture very far. That’s why we’ve broken it all down into four different day trips. Whether you’re interested in shopping, nature, dining or architecture, there’s something for everyone to enjoy.

Coming from Chicago? The North Shore is only 30 minutes from downtown and easily accessible with public transportation. Take the “L” Purple line to and from Evanston or the Yellow line for Skokie. Metra also services Evanston, Glenview, Northbrook, Prospect Heights, Wheeling and Winnetka.


Westfield Old Orchard in Skokie

Day Trip Idea #1: Shop ’til You Drop
Chicago’s North Shore has plenty of great shopping, both large and small. You can spend an entire day at Westfield Old Orchard alone. In addition to great shops like Nordstrom and must-visit dining destinations, including Maggiano’s Little Italy, Old Orchard’s outdoor setting allows you to soak up the sun while you hunt for great deals. Less than a mile away, you can check out the newest exhibits at the Illinois Holocaust Museum.

The Glen Town Center also lets shoppers stay outside on a nice day. Here you can visit Apricot Lane for the latest in women’s fashion or Cookies by Design and Oh, Olive for great gifts for your favorite foodie.



If you’re looking for a smaller shopping experience or unique gifts, head out to Winnetka and visit The Book Stall at Chestnut Court for that new best seller, Material Possessions for whimsical décor, Mattie M. for designer clothes and accessories or Oui, Madame for a gift with French flair.


Photo courtesy of the Chicago Botanic Garden


Day Trip Idea #2: Chicago Botanic Garden
No matter the time of year, there is always something to explore at Chicago Botanic Garden. But if the weather is nice, don’t just explore on foot. Rent a bike and make your way from the Garden all the way to Skokie Lagoons and various woods (Blue Star Memorial Woods, Glenview Woods, Linne Woods and more). Find a map of the trail here.

When you’re done exploring, end the day with dinner and a cocktail at Guildhall or Guanajuato in Glencoe.


Macarons from Patisserie Coralie


Day Trip Idea #3: Downtown Evanston
There’s so much to do in Evanston, you might need more than a day to explore. Whether you start or end your day with a delicious meal, don’t miss burgers and fries at Edzo’s Burger Shop, steak at Pete Miller’s or macarons at Patisserie Coralie. In addition to its great dining options, Evanston is also a bustling shopping destination. Stop by Eve Alfille Gallery and Studio for jewelry, Cultivate Urban Rainforest & Gallery or Perennials for gifts, Spice House for spices and herbs, Old Town Oil for fine oils and balsamic vinegar and Stella or Talia for clothes and accessories. Whenever you explore, make sure to schedule time to walk around Northwestern’s campus (tip: stop at the Lakefill for a great view of the Chicago skyline).

Not ready to leave? No problem! Turn your day trip into a mini staycation with an evening at quaint bed and breakfasts Stone Porch by the Lake and Stone Terrace or one of Evanston’s multiple hotels.


Evanston History Center


Day Trip Idea #4: Architecture Lovers
If you’re on the hunt for stunning architecture and beautiful buildings, you don’t need to look beyond Chicago’s North Shore. Start at the Baha’i House of Worship (a frequent destination for pro and amateur photographers) for stunning lace-like details before making your way to Northwestern, where you’ll find multiple must-see structures, and the Grosse Point Lighthouse. While you’re in Evanston, visit the Frances Willard House Museum and Archives and Charles Gates Dawes House, where you’ll find the Evanston History Center, which hosts walking tours throughout the year. 

When you’re done exploring, take an opportunity to check off another Evanston restaurant from your list.