Chicago Weekend Getaway with iBestTravel

Chicago is the perfect destination for a weekend escape, especially during the summer months. This vibrant city is bursting with culture and entertainment, including delectable food options, exquisite cocktails, rich history, stunning architecture, and a lively atmosphere filled with festivals, live music, and art. The sprawling Lakefront Trail along Lake Michigan offers an extraordinary experience for visitors. It’s safe to say that this city truly has it all.

Chicago Weekend FAQ

• When to arrive: Arrive on a Friday. To ease your stress, avoid rush hour (between 3 PM and 7 PM) to ensure a smoother commute.

• How to get from the airport: Do not, under any circumstances, take a car. The Kennedy (I-90) is perpetually congested unless you catch it very early in the morning or late at night. Instead, opt for the L, using the Blue Line from O’Hare or the Orange Line from Midway. It takes about an hour and costs between $3 and $5, depending on your destination.

• Getting around town: Try to take the L whenever possible. While some neighborhoods are conveniently close, they may be time-consuming to access via public transportation. In those scenarios, you can use Divvy bikes or catch a Lyft or Uber.

• Where to stay: Chicago boasts a plethora of neighborhoods to explore. The West Loop features trendy accommodations, while hotels along Michigan Ave offer captivating lake views. For an exceptional experience, consider staying at a highly-rated hotel with stunning amenities.

• What to pack: Chicago experiences extreme weather, so plan appropriately based on the season. In summer, light pants, dresses, and casual T-shirts are ideal. If you plan to do plenty of walking, pack your most comfortable shoes.

Friday

Arrival: After an hour-long ride on the L from O’Hare, a short walk led us to our hotel. I had pre-arranged our stay, and we were greeted with an impressive suite boasting breathtaking views of Lake Michigan.

Checking in: The suite was stunning, featuring unobstructed views of both the lake and iconic buildings. Comfort was at its peak with a cozy living area, a wet bar, and a splendid bathroom complete with a free-standing tub, adding a luxurious touch.

Al fresco cocktail hour: Feeling grateful for our beautiful suite, we toasted with Cava and enjoyed delicious gin martinis alongside friendly patrons who recommended the sushi at the hotel’s outdoor terrace bar.

Saturday

Morning and breakfast: We were greeted by another sunny day in Chicago. Our first stop was at a unique Filipino bakery known for its Michelin-starred cuisine by night. The culinary journey was indeed worth the wait, and each bite was bursting with flavor.

How to spend the day: After our satisfying breakfast, we took a walk to experience the renowned deep-dish pizza, known for its gooey goodness. Afterwards, the Chicago Architecture Center’s boat tour provided a fascinating look at the city’s skyline and rich architectural history.

Dinner: Our culinary adventure continued in the West Loop with a lively dinner in a beer hall style restaurant, known for its eclectic menu. The emphasis on locally sourced ingredients made our meal all the more special.

Sunday

Morning: Another beautiful sunrise spurred us to take a refreshing walk along the Lakefront Trail. Despite the weekend bustle, the picturesque views and delightful people-watching made the effort worthwhile.

How to spend the day: Following our exercise, we headed to a classic diner for a hearty breakfast. The menu is celebrated for its friendly service and delicious selections, making it a beloved local spot. If the Cubs are playing home, catching a game at Wrigley Field adds a quintessential Chicago feel.

Goodbye, Chicago: With fond memories in hand and a last toast at a local bar, our weekend adventure concluded, yet the experience left us eager to return to this vibrant city.