Frank Sinatra once sang that he “left his heart in San Francisco”. I can say the same about Chicago. I lived there for 3 years when I moved to the U.S., my first child was born there and I have always kept fond memories about this city. I will give you advice on Chicago family vacation from the perspective of a local, not a tourist, which may vary from standard travel tips you can get about the Windy City. By the way, regarding the notion of “Windy City”, I am not sure it is entirely true. Chicago is not windier than San Francisco Bay Area where I have been living for the past 3 years. So let’s throw away all the stereotypes, pack the bags and go!
The big question is where to stay in Chicago for a great family vacation. Often you will hear people point out hotels close to downtown and /or along the Michigan Avenue. I would tend to disagree. If you travel with kids this is not the best area to be in. It is noisy and crowded and it is the most expensive. I would recommend Lincoln Park area in Chicago, which is a little bit North of the mayhem. That’s where I lived all 3 years and I wouldn’t trade this location for anything else.
Family attractions in Lincoln Park Area of Chicago
It is relaxing and almost perfect if you travel with kids: it is located, as you may have guessed, next to a huge park along the shores of Lake Michigan with a lot of walking trails, two ponds, a beach, a FREE Zoo, and a FREE flower conservatory!! You can spend your first couple of days of your Chicago family vacation just settling in and enjoying this laid back area.
A few words about the Lincoln Park Zoo: it is a jewel among the zoos in the U.S. It has a lot of interesting exhibits that you would expect from a big zoo: polar bears, penguins, lions, monkeys, giraffes and many-many more, but it is compact in size and easily walkable. So it is engaging for older kids and adults but manageable for youngsters.
In terms of hotels I can suggest a couple in the Lincoln Park area, depending on your budget:
The Willows – located on a quiet side street (the street I used to live on 🙂 ) a walking distance from the Park. It is a moderately priced option with continental breakfast included in the price as well as cookies in the afternoon (your kids are going to love you!)
Hotel Lincoln – a more expensive option, but right across the street from the park. I believe breakfast is not included.
Family attractions in downtown Chicago
If you want to visit attractions in downtown Chicago you can do it simply by getting on Bus # 151 anywhere on N Stockton Drive which runs along Lincoln Park but you can always come back to this relaxing oasis. Route 151 passes through most of the best downtown attractions in Chicago and you can just hop on and hop off as needed. Here is the list of attractions as they are going to appear in order when you are going to travel from North to South:
- The Drake hotel (check out their fancy afternoon high tea)
- John Hancock Building with 360 degrees city observatory on 94th floor and the Signature Room restaurant on the 95th floor (this baby is a bit expensive but great for a special occasion)
- North Michigan Avenue shopping district (aka Magnificent Mile)
- Millennium Park with a horde of its own attractions (Lurie Garden, Crown Fountain, Harris Theater for Music and Dance, Great Lawn (which hosts FREE outdoor concerts in summer and strolling carolers in December, next to the Bean, and a couple of ice rinks for winter fun)
- The Art Institute of Chicago (bus # 151 last stop is next to the Millenium Park, it’s Northern corner, but the museum is just next to the park, on the South side)
- Grant Park (#151 does not stop there so you will have to walk a little bit further South from the Art Institute)
Also if you walk 1 block westwards form the last stop of bus #151 you are right in downtown (Loop) of Chicago with all the restaurants, shopping etc.
Top 4 attractions in Chicago
What is not on 151 bus route (and really there is no easy way of getting there from anywhere, unfortunately) are the Big Four attractions, as I call them: The Field Museum (museum of natural history), Shedd Aquarium, Alder Planetarium and Museum of Science and Industry. So you will have to get a taxi or Uber or Lyft. All these four places are a must see, I have a hard time even prioritizing them for you – they are all stellar. If you have only young children, probably, Shedd will be the most interesting for them. The good thing is that The Field Museum, Alder Planetarium and Shedd Aquarium are located next to each other so potentially you can do a couple of them in one day (though I would not recommend that if you have small kids, all of them are overstimulating, huge in size and take time to explore).
Museum of Science and Industry is located on the South side of Chicago on its own. It is big and comprehensive so if you decided to drive all the way there you may as well make a day out of it. This museum has permanent exhibitions, temporary exhibitions, a 3D movie theater and various unique tours and experiences. In terms of the tours, my most favorite is real U-505 boat tour. In terms of experiences, VR Spacewalk is at the top of my list, for sure. I would say this museum should definitely be at the top of your list of things to do in Chicago.
Compared to Chicago FREE attractions mentioned earlier these big museums are quite expensive but you can save a huge chunk of money by buying Chicago City Pass:
Chicago Botanical Garden
One more attraction that I am very partial to is Chicago Botanic Garden. The name is deceptive: the Garden is not located in Chicago proper but in the town of Glencoe. It is roughly 24 miles from Lincoln Park but with traffic it can take anywhere between 40 minutes to an hour to get there but it it is so worth it! It is a beautiful and serene oasis with a variety of exhibition gardens such as Japanese garden, rose garden, English wall garden and many others. It is a perfect place to get away the hustle and bustle of town. Just plan to spend a day there, take a picnic basket, 
a picnic blanket
and savor the moment (if you don’t have a picnic basket, the Garden has a good cafe serving yummy healthy dishes).
There are some famous attractions you can skip in Chicago:
- if you visited Hancock Tower, you do not need to go to Sears tower observation deck
- if you visited Lincoln Park Zoo, you definitely don’t need to track as far as Brookfield Zoo
- I would definitely skip the Navy Pier altogether. It is touristy, crowded and doesn’t add much educational value.
Organized tours perfect for a family vacation in Chicago
I am not a fan of organized tours, I like to explore things myself, at my own pace. However, in Chicago there are a couple of tours that I tried and would recommend:
- Untouchable Gangster Tour – not really appropriate for younger kids, but older kids and adults will definitely have fun. It is like stepping into a gangster movie for 2 hours, sort of. To get you prepped for the tour and the visit to the City I suggest reading this book: Capone: The Life and World of Al Capone
. It is a fascinating read about Chicago’s history. - A water cruise (either on Chicago river, Lake Michigan or both). Architectural tours are narrated excursions done on the river, they are about 90 minutes long and you can sit on either bottom (closed) or upper (open) deck. I would recommend to have this tour on a smaller boat without food included (it will be much cheaper). Lake cruises are about 2 hours long and usually employ bigger more luxurious boats (also with open and closed decks) and organized as either brunch or dinner cruises with food included in the price but there isn’t much of a narration, just some snippets of information provided here and there. Which one to choose is entirely up to you and your crew. In all honesty, I think an architectural cruise will not be too exciting for younger kids (but definitely interesting for adults). Lake cruise will be more appealing the the youngsters but it is quite pricey. It is great for a special occasion. We used Odyssey Cruise for a brunch cruise and enjoyed it a lot. As for the river cruise, we toured with Wendella Boats.
. It is a fascinating read about Chicago’s history.
When to visit Chicago
At different times of the year you can enjoy different Chicago. Here is my perspective on when is the best time to visit the city:
January and February: these are the coldest months in Chicago and probably the least pleasant. If you have a choice, I would suggest to look at other months when traveling with kids, except that if you come the first week in January you may still catch some of the Christmas events, like Winter Wonderfest, Zoo Lights, Wonderland Express, etc. (described in “December” section below) – but you will need to double check the dates before you plan your trip.
March: early March can still be cold but it is better than winter. If you are in town around St. Patrick’s day I suggest visiting Chicago River, which is being colored entirely green for the occasion. End of March – early April is also a great time to visit Morton Arboretum. I have not mentioned this attraction earlier because it is 36 miles away from the center of town and not many tourists will venture out there (you will need a rental car). This time of year Arboretum has fruit trees are in bloom as well as hundreds of daffodils and it is a magnificent sight!
April and May are great months to visit Chicago. The weather typically is nice, not too cold, not too hot and from mid April to about mid May tulips will be in bloom along the Magnificent Mile and spring blooms will fill Chicago Botanic Garden (tulips included).
June: still a wonderful time for a visit weather-wise. Starting from mid-June, FREE concerts will be held in Millennium Park throughout the summer. The schedule is usually published early April on various web sites as news releases: City of Chicago, Chicago Tribune and many others. Just use Google search.
July and August: that’s when things can get hot and humid, almost like in Florida. However, if you are tolerant to heat, there are a lot of festivals happening in Chicago this time of year, FREE concerts in Millennium Park are on-going and with a long hot streak and the right set of water current conditions lake Michigan can get warm enough to swim in! That’s when that Lincoln Park Beach will come in handy.
September and October: weather will become tolerable again, crowds will dwindle and so it’s a perfect time to visit Chicago. If you are coming in October I strongly suggest spending a day at Morton Arboretum – it is the place to be for a splendid display of fall foliage.
November: weather is getting less pleasant and Chicago won’t often come to mind as a travel destination for many people but it would be wrong! From the middle of November the Holidays Season reign supreme in Chicago. It starts with the Magnificent Mile Lights Festival (dates change year to year but it usually takes place Fri-Sun in the middle of November) that encompasses many activities: a big parade, visit from Santa, music performances, vendor/activities booths, the lighting of the biggest city’s Christmas Tree and fireworks. And if this is not enough, Chicago downtown hosts an annual Thanksgiving Day Parade (on State street from Congress to Randolph). Some other holiday events start in November too, like German Christmas Market.
December: This is actually my favorite time in Chicago, regardless of the weather, because not many cities in the U.S. do Christmas festivities the way Chicago does it. You can get complete information about December activities and events in the city in my Christmas in Chicago post.
Additional tips for Chicago family vacation:
- Schedule of various parades held in town throughout the year can be found HERE
- Schedule of Chicago festivals can be found HERE
- Try various cuisines in town. Chicago has a huge German, Polish, Ukrainian, Russian, Greek and Italian population, that is in addition to a profound Chinese population in Chinatown. I did not recommend any specific restaurants because there are so many in town depending on where you are going to stay and whether you are going to have a rental car or not but if you are going to be in Lincoln Park, don’t miss Cafe Vienna, a classic European cafe with AMAZING desserts.
- Chicago is also famous for its theater/opera productions, sporting events and concerts. To check what’s on when you are visiting just go to Ticket City end enter “Chicago” in their search box and it will show you all possible events in town and you don’t have to search each specific venue separately:
5. If you decide to visit the Windy City just with your spouse to rekindle your romance, check out these date night ideas in Chicago.
If you found my Chicago family vacation itinerary useful, please do me a little favor and share this trip with others, for there’s a good chance that it will help them with their travel plans. 🙂
