Chicago: Our Favorite Weekend Getaway

Chicago Greeters

Whether it’s your first time in Chicago or your fiftieth — or even if you live there — you absolutely need to sign up for the free Chicago Greeter Program.

This program is hands-down one of the best ways to experience the city from a unique, local perspective. A volunteer guide will take you on a personalized walking tour based on your interests, showing you both famous landmarks and hidden gems you might otherwise miss.

On our visit, we spent about three hours with our Chicago Greeter, a volunteer named Stetson, exploring the areas around Millennium Park. It was incredible to see the city through his eyes! Stetson was knowledgeable, enthusiastic and full of fascinating stories, insider tips and fun facts. He even took us inside buildings and spaces we had walked past on previous trips without realizing what we were missing. His love for Chicago was contagious — it made the entire experience unforgettable.

Tours must be reserved in advance, so be sure to sign up before your trip!

Garfield Park Conservatory

The Garfield Park Conservatory is one of the largest indoor conservatories in the nation! It is stunning and totally free.

The Conservatory offers both indoor and outdoor gardens with space to sit and enjoy the views. We spent about an hour walking through the various rooms, greenhouses and outdoor landscapes. Reservations are free and required to enter. Advanced reservations are easy to obtain using the website. Walk-up reservations are an option as long as space allows. There is a small gift shop which provides water, simple snacks and souvenirs.

The Chicago Lakefront Trail

The Chicago Lakefront Trail is an 18.5 mile mixed-use trail along Lake Michigan shoreline. We love to spend time along the trail and consider it a must-do when visiting Chicago. Visitors can walk, bike, skate or run along the trail. The trail passes through seven neighborhoods. This includes downtown, making it easy for visitors to easily access beaches, parks, favorite attractions and beautiful views of the harbor and skyline.

The trail is open 24 hours a day, but the parks and beaches close daily at 11 pm. Technically, pedestrians have the right of way, but be sure to look carefully as the bikers and skaters move fast!

Lincoln Park Zoo, Alfred Caldwell Lily Pool and Lincoln Park Conservatory

The Lincoln Park Zoo is Chicago’s only free zoo — and one of the oldest in the country. Easily accessible by bus, Metra or car, it's just a short distance from downtown and a perfect way to spend a few hours (or an entire day!) in the city.

You'll encounter lions, bears, apes, zebras and more as you explore the zoo’s beautifully maintained grounds. Don't miss the Farm-in-the-Zoo exhibit — a fun bonus that's easy to find by following the zoo map.

While the zoo itself is free, onsite parking is paid, as is most nearby street parking. There are plenty of snack stands and cafes inside the zoo if you need a quick bite or drink.

Get the most out of your parking fee by visiting the nearby Alfred Caldwell Lily Pool, located just outside the zoo’s parking entrance. This hidden gem offers a peaceful walk through landscaped gardens surrounding a serene lily pool — a quiet break from the buzz of the city.

Finally, don’t miss the Lincoln Park Conservatory, just steps away from the zoo. Admission is free (with a suggested donation), but you’ll need to reserve tickets in advance. Inside, you'll find lush indoor gardens filled with exotic plants and tropical greenery — a perfect way to round out your Lincoln Park adventure.

Millenium Park, The Bean and Maggie Daly Park

No visit to Chicago is complete without a stop at Millennium Park. This free park is located right in the heart of downtown. Often photographed, the famous Bean sculpture can be found in Millennium. The Bean (officially named Cloud Gate) is a shiny, reflective sculpture perfect for snapping some classic Chicago photos and seeing the city's skyline in a whole new way.

No matter the season, we always enjoy strolling through Millennium Park. There are hidden gardens to discover, amazing views of the city, snack shacks and ideal picnic spots — perfect for people-watching. Depending on the time of year, you might also catch a free outdoor concert or an art installation.

Right next door is Maggie Daley Park. It is a beautiful, family-friendly space with playgrounds, picnic areas, gardens and a unique skating ribbon. It turns into a rollerblading path in the summer and an ice-skating trail in the winter.

Chicago Athletic Association Hotel

Once a private, members-only club, the Chicago Athletic Association Hotel is now open to the public — and completely free to explore! Located right across the street from The Bean and Millennium Park, this historic, landmark building is absolutely worth a stop. Step inside to admire the gorgeous architecture and charm that has been carefully preserved.

During our visit, we grabbed some snacks and drinks and spent a fun afternoon playing pool in the hotel's Game Room. The hotel also features several restaurants, public restrooms, and the historic pool and locker rooms that offer a glimpse into the building's past. The Chicago Athletic Association Hotel is the perfect spot for a break between sightseeing stops downtown!

Uvae Kitchen and Wine Bar (Andersonville)

Uvae never disappoints. It’s hands-down our favorite restaurant in Chicago! This full-service kitchen and wine bar also has a nearby fromagerie & tasting room. The menu features tapas-style dishes that rotate seasonally, and we can honestly say we’ve never had a meal here that wasn’t incredible. You’ll find a great selection of wines, bubbles and cocktails. Street parking is available along North Clark or residential streets nearby, with some paid lots in the area. Reservations are recommended.

The Lakefront Restaurant (Lakefront Trail/Lincoln Park)

Located right along the Lakefront Trail, this restaurant offers both indoor and outdoor seating with stunning views of Lake Michigan. It’s easy to access from the trail or nearby beaches, making it a perfect brunch or lunch stop before or after your Lincoln Park Zoo visit or trail walk/run. Parking can be tricky — we recommend parking near Lincoln Park (street or zoo lot) and walking over. Reservations accepted and recommended, especially on weekends.

RJ Grunts (Lincoln Park)

Located just around the corner from the Lincoln Park Zoo, RJ Grunts is famous for its burgers, milkshakes and their classic "Lettuce Entertain You" salad bar. The food is hearty, the portions are generous and the vibe is fun. Parking options include nearby street parking or using the paid zoo lot. Reservations accepted.

Bourgeois Pig Cafe (Lincoln Park)

A charming walk-up café with both indoor and outdoor seating, Bourgeois Pig offers a wide variety of sandwiches with creative names like The Great Gatsby and The Beggar’s Opera. They also have delicious bakery items perfect for a quick breakfast or lunch. Street parking only. No reservations accepted.

Peckish Pig (Evanston)

This family-friendly gastropub offers cozy indoor seating and a lively outdoor patio. Serving up house-brewed beer, wine and classic comfort food favorites, it’s worth the drive up to Evanston. Street parking only. Reservations accepted and recommended.

Guinness Open Gate Brewery (West Loop)

More than just a brewery, the Guinness Open Gate location in the West Loop includes a restaurant, taproom, bakery and gift shop. While Guinness is obviously on tap, the drink list also features other beers, cider and cocktail options. Indoor seating (reservations recommended) and a spacious outdoor beer garden are available.

Recess (West Loop)

Also located in the West Loop, Recess features a huge outdoor patio space — one of the largest in the city! It’s a fun spot to grab casual food and drinks, play games and hang out with friends on a sunny afternoon or warm evening. The menu offers creative takes on classic comfort foods. Street parking is available. Reservations accepted and recommended

Skokie Baked Goods (Skokie)

This one is a bit of a drive if you’re staying downtown, but totally worth it if you're a bagel lover! Located in a strip mall in Skokie, the Skokie Baked Goods serves freshly made bagels generously loaded with “smear” (cream cheese). Add some lox and it’s absolute perfection. There’s often a line (always a good sign!), so be ready to order quickly when it's your turn. Limited parking is available in the lot.