When we lived in Chicago, we loved having our family come to visit! We hosted several family groups while we were there, and we’ve made the perfect family weekend trip to Chicago itinerary!

Day 1

Afternoon: Arrive and Get Settled

Once you arrive into Chicago, the easiest way to get to your hotel or Airbnb is to travel by Uber/Lyft. We recommend dropping off your bags and checking in if possible before taking off to do some exploring.

As always, we recommend walking around your neighborhood to get your bearings and learn about the area of town you’re in. It’s also nice to get some fresh air after traveling via plane or car.

If you’re having trouble deciding what area to stay in or which hotel to pick, check our our Ultimate Guide to Chicago coming soon to the blog!

Evening: Grab a Drink at Time Out Market

Time Out Market is located in West Fulton Market. It’s a market made up of 20+ food vendors and it features a rooftop bar. In the past, we made a night out of it, but for a quick weekend visit, we say just visit for a pre-dinner drink! Their rooftop bar is decently small, but we were able to catch a table as another couple was leaving. The indoor rooftop area is also nice, and their patio on the ground level is super fun for people watching during the warmer months. You don’t need a reservation since you purchase food and then find a communal table (food hall), so it’s easy to stop by whenever.

Night: Grab Dinner at Roister

After drinks, we recommend staying in the West Fulton Market area for dinner. There are so many great restaurant options, but our top pick is Roister. It’s great for a fancier date night, girls night out, or family visits. You’ll likely need to pay a deposit when booking but be sure to grab a reservation online, and choose the patio for some fun people watching or sit inside to watch the chefs do their thing! The open kitchen is such a cool concept, and you can’t go wrong with any of the dishes. We saw another table order one of everything on the menu and thought it was a great idea to share and try a bunch of different dishes!

If you want to make a night of it, get reservations for The Aviary before or after dinner. This fancy cocktail bar is a great treat for your night out! Owned by the same people as Roister (and Alenia, arguably the nicest restaurant in Chicago), it’s sure to live up to expectations.

If Roister doesn’t work out for you, try Beatrix, La Josie, Cabra, Joe’s Imports, or Avec. We’ve been to all of them and highly recommend! Any would make a great pick for a family trip to Chicago!

Night cap: Grab a drink at Recess

Recess is popular bar in the West Fulton Market area. You’d easily be able to walk from any of the restaurants we mentioned above. We first visited while on a trip up here when touring Kellogg before Kevin committed, and we’ve heard students rave about it since being here. From a great beer selection, to communal cocktails served in a water jug, you’re sure to find something for everyone in your group. With over 14,000 square feet of space, you’ll love the indoor and outdoor seating options. It’s a great spot for a group meet up, and the patio is dog friendly! Grab a reservation on their website or through OpenTable. It’s a $10/person no show fee if you don’t make it. Warning: this is for fun families only! If your family doesn’t like loud & hoppin’ bars, this isn’t the place for them.

If Recess is a bit too bumpin’ for your family (it does get quite crowded the later at night on weekends), perhaps check out Blind Barber speakeasy! It’s also in the area and has a nice vibe and would be fun for a family of all adults!

Day 2

Morning: Brunch in Wrigleyville

We love taking guests to Wrigleyville, and our families loved visiting it! It’s such a unique area and even non-sports fans are sure to be amused! We’ve found THE BEST spot for brunch in Wrigleyville — Swift & Sons Tavern. Swift & Sons is a steakhouse in West Fulton Market, but the Tavern is located in Wrigleyville and is a more casual environment for sports watching and fellowship. Known for its oysters and beer selection, there’s something for everyone on the menu. We sat on the second floor and the floor-to-ceiling windows were to die for. Highly recommend! Grab a reservation on OpenTable before heading there.

After brunch, be sure to walk around and take a look at the area. You might even be able to book a tour of the stadium if your group is interested. There are still many shops to hop in and out of, and there are additional bars if you’re looking for a boozy exploration day.

From Wrigleyville, we recommend Ubering into the heart of the Chicago for more exploring. We recommend getting dropped off at Cloudgate to begin your day of city exploring.

Early Afternoon: Explore Millennium Park

Cloudgate, affectionally known as “The Bean,” is the top tourist destination in Chicago. It’s a super cool sight to see and it’s a must-see for sure!

Be sure to explore the park area around The Bean, and if you want a snack with some people watching, stop at Park & Grill. Or, visit Cindy’s rooftop bar nearby for a cocktail. In the winter, this area turns into an ice skating rink.

Late Afternoon: Explore the Art Institute of Chicago

After exploring The Bean area, walk a couple blocks towards the Art Institute. It’s a beautiful walk with views of the Art Institute’s gardens. The Art Institute is quite expansive, with all different types of exhibits. From Chinese pottery, to impressionist art, to sculptures and ancient money, you’re sure to see it all. Additionally, there’s usually a special exhibit for a small added fee. When we visited with our family, there was a Monet exhibit. We purchased our museum tickets in advance since there are sometimes capacity limitations.

Don’t miss out on the Chagall windows, which are a bit hidden but worth finding. Chagall executed 86 stained glass windows across the world, and this one is especially unique due to the secular nature. It depicts the Chicago skyline, American history, and the arts.

We also added on the Monet exhibit, which sold out roughly a week before our visit. The Monet exhibit was wonderful and well worth the extra $7. But be warned that there is a virtual line to get into the exhibit which took us ~2.5 hours to get through. Perhaps visiting on a non-weekend-day would be better for timing. We’re not sure it was worth the 2.5 hour wait, but you can explore other parts of the museum while waiting.

The Monet exhibit was absolutely stunning, and learning more about the artist was quite interesting. It’s crazy that so many pieces belong to individual collectors. Can you imagine owning something so beautiful and valuable?!

Early Evening: Walk the Magnificent Mile

From the Art Institute, we left on foot to walk towards 360 Chicago (John Hancock building). It’s roughly a mile walk, but it doesn’t feel like it. You’ll walk along the scenic “Magnificent Mile,” which is home to dozens of high end shops and hotels. This is the heart of downtown and where all of the tourists flock. Along your walk, stop at the Nutella Café for a sweet treat, or stop at the world’s largest Starbucks, which happens to be a Starbucks Reserve. If you’re feeling fancy, you can reserve a table on the rooftop patio for a drink tasting. They sell both non-alcoholic coffee drinks and alcoholic coffee drinks, and they have tons of pastries and food options. If there’s a line, don’t be too intimidated because it moves rather quickly.

A great photo spot is just after crossing the DuSable Bridge towards the Magnificent Mile. We actually saw 4 wedding parties taking photos there on a Saturday afternoon in a 30 minute timespan! Above is a photo during the day and below is a photo at night. Overlooking the water and the skyscrapers, it’s such a cool view of the city.

Evening: Visit 360 Chicago (John Hancock Building)

By the time you make it to 360 Chicago the sun will be setting or already set (depending on how much shopping you do along the Mag Mile and what time of year it is… in the winter the sunsets close to 4:00!). This will allow you to have an amazing view of the city from the top of the Hancock building. There is a bar on top, so feel free to plan to stay a bit!

When we visited with my parents, we purchased tickets for a specific day but there was no required time slot. Unfortunately, the lines were backed up for roughly 3 hours so we decided not to wait. Luckily, the tickets were good for a year so I was able to use them another weekend with friends. We went on a Friday morning and there wasn’t a line then!

Night: Grab Deep Dish Pizza

You can’t visit Chicago without eating deep dish pizza. Some people will argue about which restaurant serves the best deep dish, but you can’t go wrong with either of the front runners, Lou Malnati’s or Giordano’s. Kevin thinks I’m absolutely crazy, but I can’t taste the difference! If you’re following our itinerary, there’s either walking distance from 360 Chicago.

We left 360 Chicago when we found out there was a 3 hour wait and decided to go straight to Giordano’s for dinner. Unfortunately, there was an hour wait there so we decided to Uber back to Evanston (where we live) and order takeout on the way so it’d be ready as soon as we got home. It’s worth the wait though if you’re staying in the city!

If you want a more elevated dinner experience, check out Etta, Avec, Ema, Beatrix, or RPM Italian (all their River North locations) for great dining experiences. We’ve been to them all! Finish the night with a cocktail if you wish at Three Dots and a Dash.

Day 2

For your second day in Chicago, we recommend exploring other areas! There are so many cute neighborhoods to see while in the city, so we recommend starting your day in Lincoln Park.

Morning: Brunch at Summerhouse Santa Monica

Summerhouse Santa Monica is a hip, trendy (might we say Instagram-able) spot for brunch in Lincoln Park. They’ve since combined with the pizza spot next door so we recommend calling ahead after booking on OpenTable and requesting a table in the Summerhouse portion. We love the open air feeling and think it’s a better ambiance on that side! The food was delicious and the service was impeccable.

Other options for brunch in Lincoln Park include Willow Room and Blue Door Farm Stand.

Early Afternoon: Explore Lincoln Park

After brunch, walk off some of that food by exploring the neighborhood. Lincoln Park is so charming! Every house we passed by, I was amazed by how beautiful it was. Clearly multi-million dollar homes, we had a great time people watching and imagining the type of person/family in each. Not to mention, it was around Halloween so the decorations were a fun touch too!

Afternoon: Grab a beer

There are several spots in Lincoln Park to grab a beer. We love Off Color, but if that doesn’t work out, try the Goose Island taproom. There are many other pubs and restaurants around for stops too!

Late Afternoon: Architecture Boat Tour

After our beers, we grabbed an Uber back downtown for an architecture boat tour. We highly recommend booking in advance through Wendella Tours. When I first started looking for a tour company, Wendella had the best reviews and has been around the longest (since the early 1900s!). I’ve booked three tours for three different sets of guests and have never been let down. The tours are extremely interesting and the bar doesn’t disappoint! You’re sure to learn a lot of cool facts about the city and get some amazing pictures along the way.

Pro tip: if you want a panoramic view like the one above, be sure to book a tour that takes you into Lake Michigan! It’s really cool to go through the lock system as well. Since the lake is so much higher than the river, you go through the lock and it’s really cool to experience and watch.

Evening: Grab a drink along the Riverwalk

After the boat tour, you’ll be right on the Riverwalk which is a cool pedestrian walkway along the river. There are restaurants and bars along the water, which are all super cool.

We decided to grab a drink at Tiny Tapp before dinner. There’s also City Winery along the route. I think both are seasonal and close for the winter, so perhaps try Portofino Pizza (directly under RPM Seafood shown below) if you’re going during the winter.

Night: Get Dinner at RPM Seafood

After drinks, we crossed the bridge to RPM Seafood for dinner. There are several RPM restaurants that are all delicious, and they’re part of a cool restaurant group called Lettuce Entertain You (owns Summerhouse Santa Monica too). We had amazing service and a delicious meal. I’d highly recommend eating at RMP Seafood, and be sure to snag reservations well in advance, as it books up quite quickly!

Late Night: See a Comedy Show at Second City or a Magic Show at Chicago Magic Lounge

We visited Second City on a couple occasions and loved it! We also loved taking family to the Chicago Magic Lounge for a show. Both are fabulous activities to sit and relax and be entertained.

We hope this itinerary helps when planning your visit to Chicago! Drop any questions you have for us in the comments or send us an email at hello@timeofftravelers.com. Don’t forget to follow along on Instagram (@timeofftravelers) for more Chicago content!