Your Weekend in Chicago Itinerary

 By Kelly Pawlak

Weekend Chicago Itinerary

If you and your partner are in need of a weekend away, head to Chicago! You’ll have a relaxing weekend enjoying beautiful views, drinks and food that you never knew you needed.

If you’re headed to Chicago from out of town or from the suburbs, you’re going to need to find a place to stay. There are a wide variety of hotels to choose from. Start your search by deciding which neighborhood you want to be in. If you’re looking to be in the heart of the city, you will want to look for hotels in The Loop or River North. If you’re looking for something in a quieter neighborhood, check out Lincoln Park or Gold Coast. Both areas are surrounded by some of the city's best bars and restaurants and both offer a unique Chicago experience. 

After checking into your hotel on Friday afternoon, head out for happy hour! Chicago is home to rooftop bars and outdoor patios that are the perfect place to spend summer afternoons. Check out some of Chicago’s most charming rooftops or some of the breweries located in Lakeview and Lincoln Park.

When you start to get hungry, trust me, you won’t have to wander far to find dinner. Delectable dining options fill just about every block in Chicago, but you will definitely want to look into these amazing dining options in downtown Chicago. Whether you’re looking for a casual pizza night or steak and shrimp, Chicago has the best of the best.

As the night begins to set in, watch the city begin to light up! Walk down The Magnificent Mile and over the Chicago River to take in this beautiful city. Stop for some dessert or one last drink before heading back to the hotel to rest up for a full day on Saturday.

Saturday mornings are for brunch! These Chicago brunch spots are guaranteed to satisfy you! If you’re looking for a brunch spot with a large menu, you will definitely want to head to Yolk. With classic options like eggs Benedict and creative options like breakfast mac n cheese, you will be fueled for the day.

If you don’t spend time near the Chicago River and Lake Michigan, you haven’t truly experienced summer in Chicago! Fill your Saturday with waterside activities to get a real summer in Chicago experience! 

Start off by heading down to the Chicago Riverwalk. Take in the city’s incredible architecture and riverfront restaurants and shops. If you’re looking to get on the water, kayak on the river with Kayak Chicago. If kayaking does not sound like your thing, look into one of the many river cruises offered, or just stroll along the riverfront. Whichever option you choose, you will get incredible city views. If you are starting to get hungry, stop by one of the cafes or restaurants on the Riverwalk for a light lunch to hold you over until dinner. 

Next stop: Navy Pier! Navy Pier has breathtaking views of Lake Michigan and the Chicago skyline that you just can’t miss when spending a weekend in Chicago. Start the evening by walking down the pier and allowing the lakefront breeze to cool you off. Maybe stop by the Miller Lite Beer Garden for a refreshment. When you are ready for dinner, Navy Pier has several dining options, but for a romantic dinner, you’ll want to eat at Riva. It is truly a Chicago treat that you and your partner deserve on this weekend away.

As the sun begins to set over Chicago, you’re going to want a nice place to view it. For an unforgettable view of the Chicago sunset, head to Offshore at the end of Navy Pier. Offshore is the nation’s largest rooftop and its atmosphere is hard to find elsewhere. Sit back and relax at Offshore as your much deserved weekend in Chicago comes to a close! 

With so much to do in Chicago, it is important to tailor your weekend for you and your partner depending on your interests! No matter how you choose to spend the weekend, you won’t regret your time in Chicago!