The Best Chicago Family Trip Itinerary (West Town & Beyond)

Welcome to Like a Local, our recurring series where travelers share their perfect long weekend itineraries. This time, Caroline shares a family-friendly itinerary in Chicago.

Whoops! Summer was a whirlwind, and you didn’t take the family on a trip. With fall now in full swing, you're not sure you have the bandwidth to plan a vacation. Don’t despair! As a Chicago-based mom of a seven year-old, four year-old, and 18 month-old, I took the liberty of planning all the details of your family-friendly trip to my (kind of) town.

What makes this a family-friendly trip? Two things if you ask me: accessibility and flexibility. Chicago’s Midwestern location means it’s never a cross-country trip, and it’s a direct flight from most places. You can get there by car, bus, plane, train (my personal favorite), and once you’re there, it’s both a drivable metropolis and one with loads of high-quality public transportation. Its attractions offer options to a family of diverse interests, from nature and cityscapes, to sports, music and cultural experiences.

Speaking to flexibility, my experience as a traveling parent has taught me that it pays to make Plan A one step shorter than you’d think and to have lots of Plan Bs. That’s why this Saturday-to-Monday long weekend is heavy on options and access to naps, snacks, and bathrooms (probably the title of my debut album). I’m assuming you have a car with you, but you can do almost everything listed here via public transportation, which does take more time but is lots of fun if you’re not on a tight schedule and especially if you have a train enthusiast in your party. I’ll note that the closest Blue Line stops are not accessible and therefore not a great option for strollers.

Where to Stay

I found the perfect place for your family to stay—this awesome house in Chicago’s West Town neighborhood. This fully outfitted Airbnb on a scenic tree-lined street is complete with every amenity a family could need, including a beautiful outdoor space and access to public transportation and to walkable West Town. Bring some outlet covers and a baby gate if you have really young kids, but otherwise this spot is hard to beat for a family trip with a local vibe and easy access to the city. Plus, you can park your car for free.

Day 1 – West Town/West Loop Day

Chicago is home to some absolutely incredible bakeries, and my favorite is right here in West Town—Publican Quality Bread. Everything here is delicious—I usually get the savory danish, but I also recommend the plain butter croissants, chocolate morning buns (my son’s favorite), and for the sesame lover, the infamous Danske. There’s nowhere to eat inside, so you can either grab a table outside if the weather is nice (sorry, Grand Ave is neither scenic nor quiet), or you can have your household carry-out ambassador pick it up and bring it back to the house. And remember that you’re a parent on “vacation,” so don’t forget the coffee.

Once you’ve got that butter in you, head to the nearby 9 bus that heads south down Ashland (strollers on the bus on the weekends are usually fine, I do it all the time). Get off on Madison, where you can transfer to the eastbound 20 bus, or you can take the 20-minute walk east on foot down Madison into what turns into a really cute restaurant and commercial area. Take a right on Sangamon and two blocks later, you’ll happen upon the Green City Farmers Market, West Loop edition. Let the kids pick out some fresh, local fruit and veg to stock the fridge and take on excursions, and maybe you’ll find some appealing meat you’d like to grill out back of the BnB. Bring a little cooler if you’re serious, but if you’re not in the market for groceries, you can still grab a beverage, cool off under the misters, and “relax” while the kids play at the adjacent Mary Bartelme Park.

Let’s make the next choices based on your family’s needs:

If you urgently need bathrooms, diaper changes, pumping sessions, etc., I’d hop back up to Madison Ave. Waffles has easy family diner lunch fare (and some of my favorite biscuits and gravy). Black Barrel Tavern is a cute alternative, but diapers must be changed in the event room. Afterward, you and any longer-legged kiddos can take a long, well-fed walk back home (we usually take Racine), or retrace your steps on the Madison (20) and Ashland (9) buses.

If you’d like to stick to the Madison route home and have no diapers to change/other urgent needs, consider stopping along Madison for some of my favorite places to shop (*play toy store, The Fig Tree, Madison Street Books, and my favorite coffee shop, Groundswell). Then, take the Madison (20) bus west to Ashland, where you’ll find Chicago classics like Harold’s Chicken Shack and Billy Goat Tavern. Then just hop north on the Ashland bus afterward to get back to the BnB.

If you’re willing to take the long way home, I’d be remiss not to direct you north through the Fulton Market restaurant district. (There is fun shopping in this area, including more major retailers like Anthropologie and Madewell.) In this part of town, the whole family can appreciate a delicious pizza lunch at Forno Ross Pizzeria Napoletana, young kids will relish their familiar McDonald’s while you try items from the rotating international menu at the McDonald’s Global Headquarters, or older kids/less overstimulated parents might enjoy the choose-your-own-adventure at Time Out Market. On foot, it’ll be about a 25 minute walk to get back to the BnB from this area (we usually go Racine → Hubbard → Noble)—if these restaurants sound good but you’re not up for the walk, you may want to consider the car for this outing.

You’ve made it halfway through the day - another parenting milestone complete! Time for a break at home for a nap, recharge, porch-sit, what have you. We’re trying not to overschedule, so this is guilt-free time.

If you want to venture back out, consider one of Chicago’s nearby public amenities: I highly recommend the West Town Public Library (coffee by way of Hoosier Mama), which is open until 5 on Saturdays. Eckhart Park Natatorium (coffee by way of Standing Passengers) is sadly closed for maintenance for Fall 2025, but the park and playground are still open year-round!

If you’re heading to dinner from home, I’d probably meander with the fam over to Lillie’s Q, housed inside indoor/outdoor District Brew Yards, for some laid back barbecue/brewery vibes. Or for a fancier, more adventurous meal (probably featuring older kids and certainly a larger check), it’s a short ride north on your best friend the Ashland bus to delicious Mott St. (A reservation is probably a good idea).

From the library, I’d definitely recommend Forbidden Root (super walkable, unless you count the ride your kids will be taking on the coin-operated horsey outside of Alcala’s across the street). From the park, I wouldn’t fight the temptation to grab concessions from Kim and Carlo’s hot dog stand right outside (they even have a very respectable vegan dog). If they’re closed, try Noble Thai across the street, which is very family friendly despite not having a changing table.

Day 2 (Red Line Day)

Start the new day in one of my favorite ways, with a walk to Uncle Mike’s Place. It’s perfect for a family because it’s got a killer Filipino breakfast (I recommend the Tocino and Longanisa Combo with my whole heart), but the less adventurous eater can still find eggs, pancakes, oatmeal, and more. I also think the lugaw (rice soup) that comes with your meal is fantastic baby food.

If your bulls can handle a china shop, definitely stop in to The Center for Order and Experimentation (whose sign outside clarifies “not a cult”). Here you can get a cup of coffee and shop for the cutest stationery, the most interesting snacks, and ogle candles shaped like extravagant layer cakes.

The big event for today is a day game at Rate Field. I know, I know - the far more famed tourist attraction around here is the friendly confines of Wrigley Field. But hear me out—White Sox tickets are way, way cheaper, the stadium is typically less crowded, and the staff treated my family like royalty when we last attended - even though we were decked in our hometown Kansas City Royals gear. It’s such a great experience, and the tickets are so affordable that if your kids only last a few innings before naptime, you still feel like you got your money’s worth. If your family can handle a long excursion, I recommend taking the Grand (65) bus east and then transferring to the southbound Red Line, which you’ll ride until you get to Sox-35th. If you prefer to drive, we usually park with the nice lady who lives at 33rd and Shields, but you can get a good deal on stadium parking since it’s a Family Sunday.

(If you absolutely must do Wrigley, just go north on the Red Line from Grand up to the Addison stop. If you drive, it’s trickier to find parking but can be done.)

If your family can’t do a baseball game or if the Sox have tragically not advanced to late season baseball, don’t sweat it. One of the best parts about your BnB is that it is nested right between the Chicago (66) bus on the north side, which is a direct shot to the Hancock Tower area and all of the fun Mag Mile shopping and activities. On the south side, you have the Grand (65) bus, which can also to take you to Michigan Ave (though you’ll have to cut through Nordstrom in order to avoid stairs with a stroller), the touristy but excellent Chicago Children’s Museum at Navy Pier, or the pricey but honestly fantastic Architecture Boat Tour.

If the weather is poor or if you have a family of indoor cats, you might enjoy making keepsakes at Build-a-Bear, a super luxe kids boutique-shopping experience at Lola and the Boys, a photogenic visit to the Museum of Ice Cream, or a movie at Block37. If you’re looking for lunch in the area, you can find a wide selection of quick options at Goddess and the Baker or Eataly, and if the kids need some park time, choose Seneca Park for playground equipment and Washington Square Park for room to roam. I recommend rounding out your downtown time on the north side of Michigan so you can grab coffee or soft serve from Ralph’s Coffee or relax with a scoop at the most beautiful Jeni’s Ice Cream location on Wabash.

For bathroom/pumping/air-conditioning breaks, there are multiple malls along Michigan, like 900 N. Michigan Shops, Water Tower Place, and The Shops at North Bridge. Based on what appeals to you, I’d map your route in advance so you’re not needlessly going back and forth down Michigan.

However you decided to spend your afternoon, hop on the Red Line to the Cermak stop, where you will find one of the greatest Chinatowns in the country! I recommend eating at MingHin Cuisine, an absolutely palatial bastion of delicacies from every section of a Chinese food menu. I’m partial to the dim sum menu, but there’s truly something for everyone. If you’ve got nothing left in the tank and have got to get back to the BnB, you can get it delivered from the Streeterville location.

Once you’ve caught the Red Line back to Grand and taken the Grand bus back to the BnB, you’re probably exhausted. If you’re co-parenting, I highly recommend a tag team situation in which one true soldier handles bedtime while the other adds to their step count with a quick trip to Lush Wine and Spirits. Pick up something yummy to sip on while relaxing on the back porch after the kids fall asleep.

Day 3 (Flexible Day)

I like to keep the last day of a trip pretty low key. Start with a leisurely walk up to Standing Passengers, which has really good coffee, breakfast tacos from Cafe Tola, and my favorite donuts in town from Do-Rite (the chocolate old fashioned is heavenly) all under one roof. This could be a carry-out run if you prefer to avoid vintage video games for your kids, but otherwise I hope you’ll spend some time owning them in Mario Kart.

I hope you’ll consider using this time for any other options you weren’t yet able to get to!

If you’re looking for other ideas, I think you’ll love a visit to Commercial Club Park. It’s a favorite of mine thanks to its inclusion of some really tiny playground equipment that feels safer for extra little boops; Snowberry Park is also a hidden neighborhood gem. If the weather is poor, you’ve got a great option in the aforementioned West Town Library or some fun local shopping at RR#1 Chicago, Paperish Mess, or SemiColon Books.

I recommend grabbing lunch in sandwich/charcuterie form and cute market goods to-go from Tempesta Market. You could easily take it home to eat in the comfort of your BnB, or this also makes a yummy lunch to bus-accessible Ohio Street or Oak Street Beach (less crowded on a weekday!) If you’re not looking for a lot of time outdoors, try the northbound Ashland bus to the westbound Diversey bus for an afternoon at the Diversey River Bowl.

If the weather is not nice, I have a car-trip recommendation for you, involving places that are wonderful but not easy to access via public transportation: Honey Butter Fried Chicken (which has amazing fried chicken, and kids eat free!) and Climb Zone, my 7 year-old’s favorite place on earth, with complete climbing walls, a huge playground, and a soft play area for toddlers.

However you’ve decided to spend your last day in town, head back to the BnB for a low key dinner. Grill up any proteins you scored from the farmer’s market, or order in—I recommend my favorite Italian sandwich in the city from Humboldt Haus, my favorite local slice from Professor Pizza (they have halal beef!), or the delicious and iconic burger from Small Cheval, For dinner out, it’s a short walk to Mart Anthony’s, a family-friendly Italian place with a stunning patio. Alternatively, Butterfly Sushi has a large menu of pan-Asian crowd pleasers, and the stunning presentation of their dishes will surprise and delight!

If you’re up for the effort to procure the treat you have earned for executing the best weekend of your kids’ lives, it’s a long but beautiful family walk from Chicago Ave → Paulina St → Division St. for an Italian ice at outdoor Vinny D’s or an inventive indoor soft serve at Kurimu. But a vanilla soft serve at Burger Baron will do in a pinch.

I hope this loose guide has convinced you that Chicago is a great place to visit with your family. We truly love this city and have found it to be a very friendly place for families to visit, as well as live! I guess they don’t call it “that toddlin’ town” for nothing. See you around the neighborhood!