The ultimate Chicago weekend getaway guide

Chicago’s downtown, parks and lakeside are ideal for a short break. This guide will help you plan the ultimate weekend in Chicago. From the best places to eat and drink to must-see attractions, you'll find everything you need to make your Chicago weekend getaway special. So grab your camera, pack your bags, and let's explore the Windy City!

Arriving in Chicago

Start your weekend off on the right foot by arriving in Chicago! Whether you're coming from another city or country, there are plenty of ways to get here. Once you've arrived, you'll be ready to begin exploring all the incredible things to do in Chicago.

From its bustling downtown area to its waterfront views and parks, Chicago is an ideal destination for a weekend getaway. Start planning your Chicago weekend itinerary today, and you won't regret it. Don't forget to look into the best transportation options for getting around the city – from buses to the L train, your chicago travel itinerary won't be complete without it. Enjoy your stay and have a great time exploring what to do in Chicago at the weekend!

Where to Stay

Chicago is a vibrant city with plenty of hotels to choose from. Whether you’re looking for luxury or budget, there’s something for everyone.

If you’re looking for premium accommodations, the Waldorf Astoria Chicago is an excellent choice. Located in the Gold Coast area, the hotel has recently renovated guestrooms and suites for the ultimate Chicago experience. Another fantastic option is the Four Seasons Hotel, located in the heart of the city. With its chic interior, Michelin-starred restaurant, and rooftop pool, you’ll be sure to have an unforgettable stay.

For a more affordable alternative, check out the Wicker Park Inn. This charming bed & breakfast is located in the hip Wicker Park neighborhood and offers unique rooms with period furniture and decor. No matter what you decide, you’ll be able to find something that fits your budget while having easy access to all the things to do in Chicago on your weekend itinerary.

What to Eat and Drink

When it comes to things to do in Chicago, you can’t overlook the amazing food scene. Whether you’re looking for classic Chicago-style deep dish pizza, a fantastic craft beer selection or something more unique, Chicago has something for everyone.

Start off your Chicago weekend itinerary with a visit to Lou Malnati’s Pizzeria for their famous deep dish pizza. Or check out Small Cheval for their amazing burgers. If you’re looking for something more unique, explore the various ethnic neighborhoods such as Chinatown or Greektown for some authentic dishes. And don’t forget to try a craft beer at Revolution Brewing or The Beer Temple.

Make sure to include some of these amazing spots on your Chicago travel itinerary to get the full Chicago experience. Enjoy!

Friday

Kick off your weekend getaway in Chicago with a visit to one of the city’s world-renowned museums. Spend the morning exploring one of the many renowned institutions such as the Museum of Contemporary Art or the Adler Planetarium.

Afterwards, head to Millennium Park for lunch and enjoy some of the incredible things to do in Chicago at the weekend. There, you’ll find numerous walking paths and gardens, a skating rink, and interactive public art installations.

Once you’ve had your fill of Millennium Park, check out the Magnificent Mile – Chicago’s most popular shopping destination. Peruse upscale boutiques, marvel at the architecture, and take in all that downtown has to offer. Afterwards, take a stroll along the lakefront, where you can catch a glimpse of some amazing sunset views.

For dinner, sample some of the city’s renowned cuisine and continue your Chicago travel itinerary with a late night show at Second City or The Vic Theatre. No matter what you decide to do on your Chicago weekend itinerary, Friday is sure to be an adventure!

Saturday

You’re halfway through your Chicago weekend getaway, and there’s plenty to do! Begin your day with a hearty breakfast at Yolk, located in the heart of the city. Afterward, set off on an adventure around the Loop and explore some of Chicago’s most famous sites.

Follow the Chicago Riverwalk, which is lined with restaurants and shops, and be sure to snap some photos of the stunning architecture along the way.

In the afternoon, take in the views from the top of Willis Tower’s Skydeck or experience interactive exhibits at The Field Museum. For dinner, consider visiting Girl & The Goat for some creative and delicious cuisine.

To wrap up your Saturday night, head to a comedy club or music venue and soak in the unique energy of the city. With its countless things to do in Chicago on a weekend itinerary, you won't be disappointed!

Sunday

After spending two fun-filled days exploring the city, it's time to wrap up your weekend getaway in Chicago. There are plenty of things to do in Chicago at the weekend, so make sure you make the most of your last day!

Start off the morning with a walk along the Navy Pier, grabbing a coffee just as the stores open. Afterwards, explore some of the cultural and historical attractions like the Art Institute of Chicago or take a tour of the city’s iconic architecture.

Wrap up the evening with a leisurely stroll along the lakefront. Don’t forget to pick up some souvenirs or snacks to take home with you.

Top tips for a weekend in Chicago

• Make sure to check out the many things to do in Chicago, from sightseeing and attractions to shopping and restaurants.

• Try to plan your Chicago weekend itinerary in advance to make sure you don’t miss out on anything.

• Take advantage of free attractions and activities that are available throughout the city.

• Take a walking tour or hop-on-hop-off bus tour to get an overview of the city.

• If you’re looking for something a little more adventurous, consider booking an airboat ride or taking a bike tour.

• Consider signing up for a food tour or Chicago travel itinerary to get a real taste of the city.

• Take a day trip outside of Chicago to explore the surrounding area and its attractions.

• Don’t forget to check out what to do in Chicago at the weekend, such as outdoor movies, festivals, and music events.

• Make sure to try out some of the local cuisine – there’s so much great food to discover!