Tips to planning your family trip to Chicago

When it comes to traveling with kids, not all cities are created equal. Luckily, Chi-Town is one of our favorite kid-approved metropolises, offering loads of fun for the whole family. From the towering T-Rex at the Chicago Field Museum to the Penguin Cove exhibit at the Lincoln Park Zoo, the Windy City is a generous host to kid-friendly adventures. Keep reading for tips on planning your family trip to Chicago.

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Essential Items to Pack

Strollers: While Chicago is a fantastic kid-friendly city, it’s still a busy place, and you may need to adjust your plans to accommodate young children. For example, the layout of Chi-Town makes walking through the city a tourist’s dream. But it’s still a busy metropolis with lots of traffic, distractions, and the typical hustle-bustle of a big city. So avoid mishaps by packing a stroller or baby carriage so you can explore Chicago while keeping your tiny tots safe.  Ideally, pack a stroller with an umbrella or enclosures to shelter young ones from the city hubbub.  

Comfortable Shoes: While Chicago has phenomenal public transportation, the hot spots studded throughout the city are easy to get to by foot. With this in mind, be sure to pack good walking shoes because even if you stick to taxis or the L Train, you and the family will have to hoof it in Chicago.

Pack for the Season: What you take on your family trip to Chicago depends on what time of year you go.  Summertime is the most popular because the city gardens are robust, and the temperatures are ideal for a Chicago boat tour or a splash in Lake Michigan.  If you launch your adventure in the Summer, remember that it can get hot and sticky in the city, so pack cool clothing and forget the sunscreen. Spring and autumn pose cooler temperatures and chances of rainfall. These seasons can also be unpredictable, so your best bet is to pack with layers in mind; take sweaters or jackets that can be easily shed and stuffed in a backpack.  If you and the kids opt to brave the winter in the Windy City, bundle up because it gets cold. Take coats, gloves, hats, and good winter boots.

What to Know When You Go to Chicago for a Family Trip

Age-Appropriate Attractions: Chicago offers endless adventures for kids of all ages. Many attractions feature a mixture of options that appeal to adults and children alike. For example, the Lincoln Park Zoo offers engaging activities and exhibits the kids will love and also caters to parents by serving local craft brews, or you can even attend a cocktail-making class on the zoo grounds. The Shedd Aquarium and Millennium Park are also good options as they are entertaining for young minds and also engaging for adults.

Budget-Friendly Options: If your family is vacationing on a budget, you may want to invest in a Chicago City Pass.  The Pass will save you 53% on gate prices at attractions such as Skydeck Chicago, the Museum of Science, Adler Planetarium, or the Field Museum.  An alternative to a Pass might be the Go Chicago Card.  It offers similar discounts with a 55% savings on many attractions that may not be included with the Chicago City Pass.  Another savings option is the For the Explore Pass.  The discount is 40% off gate entry prices, and you’re limited to three to five attractions.  Go to the city of Chicago’s website to get the details on the many pass options available and pick the one that best fits your family’s budget and travel goals.

Eating Out: There are tons of family-friendly restaurants, eateries, and yum-shops in Chi-Town. For example, your kids will swoon over Marie’s Candies; their Atomic Sundae is so sensationally sweet, you’ll be searching for dentists in Plainfield IL! Or try RJ Grunts close to Lincoln Zoo for kid-centric meals served on retro cafeteria trays. Wherever you choose to sample the local cuisine, remember that restaurants can get busy early. Avoid crowds by making reservations whenever you can. If that’s not possible, try to plan dining excursions during off-peak hours or go early before restaurants get packed.

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Make Early Reservations: Depending upon when you are planning your family trip to Chicago, do yourself a favor and book early.  The earlier you get your airfare and hotel reservations the better your odds for getting premium amenities at a cheaper rate. Remember that summer is a popular time for tourists, so if you’re going in the summertime, make early reservations to avoid missing out on the accommodations you and your family want.

Get Tickets Online Beforehand:  Chicago is known for famous attractions, museums, and entertainment venues.  Whenever possible, buy your tickets online and in advance.  Chicago’s art festivals, music events, and beloved tourist attractions fill up fast during the peak travel season. So getting your tickets before you go will ensure you and your family have top spots at events and attractions. Buying tickets beforehand will also help your family avoid long lines and waiting to get into your desired destinations.

Remember the Golden Rule

Planning your family trip to Chicago is crucial to having a great time in the Windy City. But don’t get so caught up in strategy that you forget the golden rule: Have fun! No matter which exciting attractions you and the kids visit, always remember to stay safe and have a jolly good time while you make lasting memories during your family trip to Chicago.

Chicago Field Museum tips

We love natural history museums and have visited versions of them all over the country. The Chicago Field Museum is in our top five! We loved this cavernous, elegant museum situated on the Museum Campus by Lake Michigan and Shedd Aquarium. Here’s what we recommend seeing and doing, plus tips to plan your visit:

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What not to miss:

If you have older kids or teens, the top two or three exhibits may be the Inside Ancient Egypt exhibit, the Mastodons and Mammoths exhibit (extra ticket required), and the Evolving Planet exhibit. We also really loved the Ancient Americas exhibit. The Egypt exhibit hall starts at the main level, but staircases lead both upstairs to get a view of a tomb from the top and downstairs, where to bulk of the artifacts can be found. The best place to enter is on the main level, to get the full experience of walking through the tomb first.

Note: There are mummified remains on display, including the remains of children and infants (and cats and birds). These artifacts were amazing, but I did give my kids a heads-up.

The Evolving Planet exhibit is the primarily exhibit with dinosaur fossils, so this area will appeal to all ages, but the actual exhibit goes even deeper, which is why I recommend it for older children. It chronicles multiple ‘extinction events’ throughout history, starting billions of years ago, and is fascinating in its scope of time.

For younger kids, the multiple halls of mammals, which takes up the entire left side of the main floor, will be popular, as well as the North American Indians section and the Pawnee Earth Lodge. We were lucky enough to step into the Earth Lodge while a museum docent was on duty, and she explained all the artifacts inside, many of which kids can touch and play with. The temporary Underground Adventure (extra ticket required) is lots of fun too; after being ‘shrunk’ to 1/2 inch size, kids can walk through a soil landscape and see ‘life-size’ bugs, worms, roots, and other life in the soil. Think Honey I Shrunk the Kids.

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Everyone will want to see ‘Sue’ the T-Rex that has been making its way slowly across the country. We saw it about seven years ago in Portland, Oregon. It was fun to see again. There’s enough to see and do to spend at least 3-4 hours in the Field Museum, and possibly more. You can re-enter with you ticket if you want to take a break in the day and return. A few tips:

Check the Field Museum website’s calendar before arriving:

The Field Museum offers a number of free days, which may or may not work in your favor. During our visit, it was a free day of residents of Illinois. Since we are not residents of the state, a free day only means a crowded day for us, without the benefits. Normally, I would avoid free days that do not apply to us. However, the day we visited also happened to be a game day for the Chicago Bears, played directly adjacent to the museum. This worked in our favor, as long as we timed our bus ride to avoid the fans pouring into the stadium. The Field Museum was almost empty when we arrived at opening, and stayed light on crowds all morning, until the game ended at 3 pm.

Decide what ticket option is best for you:

The basic entry price gets you into all the regular permanent exhibits. To access the ones noted as ‘ticket required’ or to view one of the 3-4 3D movies showing, you’ll need to upgrade to either an All Access Pass (gets you into everything) or a modified all access, which allows you to chose a few extra items to do. If you plan to be in Chicago long enough to visit at least two other attractions participating in the Chicago CityPass, I recommend getting this pass before your trip or at your first stop. The Chicago CityPass is $96 for adults and $69 for kids, and gives you an all access pass to the Field Museum, plus entrance to Shedd Aquarium next door and the SkyDeck at Willis (Sears) Tower, as well as several other attractions.

Dining options in the museum:

There are two dining services in the museum. We ate at the Field Bistro, which serves healthy options like soup, salads, and sandwiches, as well as some samples like hot dogs and burgers. Downstairs, an even more casual option has more ‘kid’ foods, like chicken fingers. We were told there are food trucks at the lower level as well, though we did not see them during our trip.

Outside the museum, families can find several hot dog carts, one of which is located between the Field Museum and Shedd Aquarium.

Tip: Find more things to do with kids in this guide to 25 top things to do in Chicago!

Hours and admission:

As described above, there are several admission levels. Basic admission is $18 for adults and $13 for kids. The Discovery Pass is the middle level, and is $25 and $18. The All Access is $31 for adults and $21 for kids. Hours are listed here.

Getting there:

The Field Museum is located on the Museum Campus, just south of downtown. It’s an easy metra bus ride on the 146 from Magnificent Mile or State Street (it took us about 15 minutes on a single line from State Street in the River North district). As noted above, it can be busier if there’s an event at Soldier Field. You can also drive, but prepare to pay for parking.

Where to stay in Chicago: Westin Chicago River North

The moment we entered the elegant lobby of the Westin Chicago River North at the blustery, snowy start of our winter Chicago weekend, we felt awash in warm and hospitality. While our hands and feet warmed up quickly, that cozy feeling never went away. For the entirety of our two night stay, we were met with smiles, helpful staff, beautiful surroundings, and convenient amenities. Here’s why we’ll definitely be back:

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Westin Chicago River North provided impeccable service and hospitality from start to finish. Every question we had was answered promptly and competently, our room was spacious and had everything we needed, and the location was ideal for a fun weekend in the city.

We stayed on the 9th floor, with wonderful river views. We had a double with a full bath and shower, plenty of sink and counter space, and a spacious closet. WiFi is free for SPG members (free to join) and we had robes and a large flat screen TV with plenty of free channels so we could settle down comfortably during the chilly nights we visited. Out our window, we could watch the snow fall on the the Chicago River and enjoy the skyline.

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River North has a club level lounge, which we took advantage of. For an added fee to your nightly rate, guests can access this lounge on the 20th floor, which puts out a full breakfast every morning, snacks during the day, and appetizers and small plates in the evening. All day long, a fridge with soda, water, and other non-alcoholic drinks are on offer. We find that with a family of five, this upgrade is always worth the money. Our rule of thumb: if we’ll be at the hotel to enjoy breakfast and at least one other trip to the lounge per day for snacks, the value is there. During our stay, the lounge put out several appetizers, cut veggies and dip, fruit, cookies, and a soup of the day each evening. We found this to be more than enough for us for dinner. At very least, it’s enough to feed the kids before having a dinner out for the adults. Wine and beer is also available in the lounge for an added fee. Other guests can also use the lounge, during which they pay $15 per visit per person. (Don’t do it this way…it won’t be worth it!)

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From the River North property, we were only two blocks from the CTA lines we needed both for the train and the bus. We could easily visit the Sears (Willis) Tower, Millennium Park, and the Museum Campus (all in different directions) within 15 minutes by public transit. We loved being right on the river for a genuine Chicago feel. Note: Chicago’s CTA (Chicago Transit) is different than the Metra (short for Metropolitan Rail), which services the suburbs.

Special Westin touches:

I love Westin’s StayFit program, which allows you to rent exercise clothing and shoes for only $5. The gear is clean and stylish, and saves me room in my carry-on bag. The exercise facility on site is convenient and contemporary, and while not terribly large, it met my needs just fine.

Westin also provides a SuperFoods menu among their room service offerings in many hotels, including River North. Anything I can do to stay healthy and eat well during a trip, I’m grateful for!

I can’t say enough good things about the Westin River North concierge desk. During my stay, I was helped by three concierge staff members, and all three were excellent. I got wonderful recommendations on what to do in the city, then very specific directions when I needed them, and a swiftly called cab exactly when necessary (at oh-dark-thirty for a trip to the airport). Trust me, this doesn’t always happen!

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The front desk staff at River North always greeted us with a smile, asked if we needed any bottled waters before heading out in the morning, and had infused water on hand in the lobby. Bowls of fresh fruit were abundant, and every public space was clean, well-lighted, and welcoming. When we returned after the end of a busy day in the city, we felt the sanctuary of a home away from home.

Rates:

Nightly rates started around $150 at the time of our visit (non-holiday weekend). Upgrading to club level was an additional $50 per night, which would definitely pay for itself.

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Location:

The Westin River North is located at 320 N. Dearborn. We arrived from O’Hare, and took the Metra train Blue Line easily to the property. Valet parking is available if arriving by car.

As I disclose whenever applicable, we were hosted at Westin Chicago for the purpose of review. All opinions are our own.

Photo credit: Amy Whitley, Westin

24-hour Chicago winter itinerary with kids

On a snowy November weekend, my youngest son and I found ourselves in Chicago. Our trip there was accidental; we had been en route to Savannah, Georgia when we became stranded at O’Hare during the first snowstorm of the season. After 30-plus hours trying to continue our planned itinerary, our flight was cancelled and rebooked two days later. Rather than sit around waiting to depart, we decided to enjoy a Chicago winter itinerary. Here’s what we did with 24 hours in Chicago:

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Morning: Head to the Museum Campus

Captain Obvious alert: Chicago in winter is cold! Rather than brave the weather all day long, start your itinerary with an indoors activity. We took Metra to the Museum Campus, which houses both The Field Museum and Shedd Aquarium. Families will want to budget at least three hours for each. Because we wanted to spend some time outdoors enjoying the wintry atmosphere as well, we opted to visit just one indoor attraction—Field Museum—but if you’d rather spend all day indoors (or the weather necessitates it), you could happily spend all day on the Museum Campus, checkout out both attractions.

We chose to visit the Field Museum for its temporary exhibits, including an excellent exhibit on Ancient Egypt and on Mastodons and Mammoths. In order to see these, we upgraded from a standard entrance fee to a full access pass, a difference of approximately $10 per person. With this pass comes admission to the museum’s 3D movie options as well. We started downstairs, checking out these special exhibits first, then moved our way up the museum to end with a 3D movie (check movie times when you enter). Favorite stops among the permanent exhibits included the mammals section and dinosaur section (which has a focus on extinctions during the ages).

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We spent all morning enjoying the warmth of the museum, then ate lunch at the museum bistro, which had many healthy options, including a full salad bar and specialty sandwiches and soups. Alternatives include classic Chicago hot dog carts outside and—we were told later—food trucks on the museum ground floor.

Afternoon: Ice skating at Millennium Park

From the Museum Campus, we used the pedestrian underpass to access the nearest Metra bus stop, and took a bus back toward downtown to Millennium Park. We used Google Maps to find the correct bus lines for both the ride to and from the Museum Campus, and had no trouble using the system. If paying cash, our rides were $2.50 for adults and $1 for kids, each way.

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At Millennium Park, the McCormick Ice Skating Rink is only about half a block further on foot. On the Sunday before the Thanksgiving holiday, the rink was crowded, but not unmanageable. Plus, the snowy weather added charm to the experience! We waited in line approximately 25 minutes to rent skates (they have a timed system here, so not too many people are crowding the rental area and rink at one time). Once on the ice, we could skate indefinitely. We enjoyed the rink for about 45 minutes, then took a break at the Warming Hut, which serves hot cocoa with a full hot cocoa ‘bar’ (toppings include several kinds of marshmallows, chocolate shavings, candy bar crumbles, and syrups), plus tea and coffee, to which liquors can be added. The hut has a padded floor, so there’s no need to take off skates while warming up.

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We continued skating about 30 minutes or so, then unlaced so we could climb the stairs above the rink to check out the famous Chicago ‘bean’ sculpture, which overlooks the skating area. It was fun to see it reflecting the snowy Chicago landscape! We didn’t see much else to do outdoors in the immediate vicinity, but were told that had we been there just a week or so later, the ‘ice skating ribbon’ at adjacent Maggie Daley Park would have been open.

Early evening: City lights

Twilight hit the cityscape at approximately 4:30 pm, and we made our way back to the Metra stop to take a bus to Sears Tower (now called Willis Tower). The SkyDeck allows visitors to enjoy amazing views of the city from the 103rd floor, and even step out onto a glass floor for a thrill. Because we weren’t in the city long enough to warrant buying CityPass (more on this below), we had an hour wait in line for the SkyDeck (including the security line). We loved the views of the city with lights aglow, but agreed the wait was too long. There are two alternatives:

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1. Buy CityPass tickets. We always buy CityPass when we visit participating cities, but our visit to Chicago was just too short this time around to make it worthwhile financially. However, if we’d even had one more day, we would have bought the tickets, which are approximately $95 for adults and $69 for kids, and allow entry to 5-7 attractions. With CityPass, families skip the majority of the queue at all attractions, and CityPass holders we saw at Willis Tower enjoyed very little wait time.

2. Head to Hancock Tower instead, and eat a meal at Signature Room on the 95th floor. I’m told the views here are just as amazing, and while you do need to purchase something to eat or drink to enjoy it, the price is less than SkyDeck. Unfortunately, during our visit, a small fire caused the building to close.

Evening: Dining in or out

I polled my favorite Midwest travel writers when I realized we’d be spending a day in Chicago, and they offered several great dining recommendations. Topping the list is Eataly, an upscale but fun Italian dining experience that even includes a Nutella bar. Eataly can be found at 43 E. Ohio. Other top picks are Pizzeria Due at 619 N. Wabash and Flo and Santos at 1310 S. Wabash. Where did we go? Back to our hotel to cozy up with room service! We loved ending our day in Chicago in our robes, looking out our window to watch the Chicago skyline.

Deal: Save up to 53% on Chicago’s 5 best attractions with CityPASS. Shop Now!

Alternate ideas for a Chicago winter itinerary:

While we couldn’t get to everything we wanted to during this trip, the following additional winter activities are on our radar for next time.

  • Museum of Science and Industry: This year, this museum is hosting an amazing robot exhibit called Robot Revolution, which cutting edge robots around around the world kids can interact with. During the holiday season, it also features Christmas Around the World and Holidays of Light, which depicts holiday traditions from dozens of countries and cultures.
  • Christkindl Market: This annual German Christmas market is held on Daley Plaza, with traditional wooden huts and vendors from Germany.
  • A Christmas Carol: This show is also an annual tradition and almost always a sell-out, so get advanced tickets for the Goodman Theatre.
  • Zoolights: Held every holiday season, Zoolights at Lincoln Park Zoo showcases light displays across the zoo in the after-hours; families can come during daylight to see the animals and stay for the light show.
  • Navy Pier: Though a different experience than during the warmer months, Navy Pier has events and attractions open year round. Pick a day that’s not too chilly to be directly on the water. During our visit, it was simply too windy for us to feel comfortable at Navy Pier!

Where to stay: Westin Chicago River North

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We stayed two nights in complete luxurious comfort at Westin Chicago River North, which offered the perfect downtown location for our adventure. Our room on the 9th floor overlooked the Chicago River, and we loved watching the snow fall on the water and bridges. We upgraded to club level, which allowed us to use the club lounge on the 20th floor included in our stay. While an initial investment, I always recommend upgrading to club or concierge level when available. Most offer a complete breakfast service, plus snacks and drinks available all day and an appetizer and small plates spread in the evening to easily feed children and even adults (depending the day’s offering). If you’ll be at the hotel enough to take advantage of at least the breakfast and one additional stop-in during the day or evening, the value is there.

From O’Hare airport, the Westin North River is only one metra train line away (blue line from O’Hare), plus a two block walk. It’s also only two blocks from the metra bus lines. The views are amazing, and the concierge desk is invaluable when planning a last minute itinerary!

Photo credit