Planning your Chicago babymoon?
As someone who has spent her whole life in Chicago and is now raising my child here, allow me to be your guide!
I’ve made sure to include the best food to eat, sights to see, and shows to experience in this itinerary. I did many of these same activities while pregnant myself.
Let’s dive right in and get you babymoon-ready.
Your Chicago Babymoon Itinerary: Quick View
Chicago is full of iconic sights and can’t miss views – there’s something for everyone in this 4 day Chicago babymoon itinerary. Here’s a quick overview:
Day 1: Coffee in West Loop, Magnificent Mile, Millennium Park, Second City
Day 2: M. Henry Cafe, Clark Street, Big Jones, Chicago Magic Lounge
Day 3: Water Taxi, Chinatown, Architecture Cruise, Emily Hotel Rooftop
Day 4: Prenatal massage, Willis Tower Skydeck
The Best Chicago Babymoon Itinerary: Full View
Below is my jam-packed Chicago babymoon guide! Let’s get into it:
Day 1
Coffeeshop and Pastry Tour
Even if you’re avoiding caffeine or limiting it while pregnant, the coffee scene in Chicago is one worth exploring – if for nothing else than the delicious pastries!
Sawada Coffee in the West Loop is one of my favorites. Try their iced vanilla latte or signature military latte. You can also go straight to their cookies, I’m not judging.
I recently had the blackberry oat crumble and it was the best cookie I’ve ever purchased.
If you’re more of a croissant person, The Good Ambler is just a 5 minute walk away and has some of the most mouthwatering pastries in the city.
Both coffeeshops have lots of seating in case you want to settle in for a slower morning.
If you have the time, two other chai/coffee shops on every Chicagoan’s radar right now are:
- Swadesi Cafe, also in the West Loop – The samosa croissant has got a kick but is so YUM
- OUD Coffee & Cafe in River North – Dubai chocolate, anyone?
Magnificent Mile
Chicago’s Michigan Avenue, also known as the Magnificent Mile, sits in the heart of the Loop. It does get a bit touristy but that doesn’t take away from its beauty and all that the street and surrounding area have to offer.
The opportunities to shop and dine are endless. You’ll also bump into various gardens and the infamous Millennium Park as you stroll along this iconic street.
Picnic at Millennium Park
As you walk along the Mag Mile, pick up a picnic lunch that you can enjoy at the Pritzker Pavilion inside of Millennium Park.
Seating is easy to find on the Great Lawn but if you’d rather picnic in chairs, head to the nearby Chicago Riverwalk and hang out on the Adirondacks instead.
Other options in the area:
✨ Cindy’s Rooftop – Right off of Millennium Park, located at 12 S. Michigan Avenue, you’ll find Cindy’s Rooftop which offers one of my favorite views of the city. They have a delicious mocktail menu too!
✨Palmer House – The Palmer House is a Chicago landmark and one of the oldest, continuously operating hotels in the U.S.
The ceiling fresco by French painter, Louis Pierre Rigal, is reason enough to visit but if that doesn’t get you maybe the fact that they invented the brownie here will!
It’s still on their menu and worth a taste.
Dinner at the Purple Pig Restaurant
Over the years, I’ve heard only good things about this Michigan Ave gem that also has a Michelin Guide Bib Gourmand rating.
Second City Show
If you have any energy left, I highly recommend a Second City show.
Second City birthed and popularized improv in Chicago starting in the late 1950’s. I’ve gone to many shows and it’s one of my favorite places to take those visiting town.
Insider Tip: Opt for an earlier show if you prefer to avoid rowdy, late night comedy club go-ers.
Day 2
Brunch at M. Henry Cafe
Now that you’re a bit more familiar with the city, explore a different neighborhood on your second day in Chicago.
Andersonville has so many good eats and fun activities to offer. Head over and start the day with brunch at M. Henry Cafe. I’ve been eyeing their Lemon-Raspberry French toast for a while now.
Stroll along Clark Street
Clark Street lies in the heart of Andersonville and is home to a ton of cute local shops, cafes, and restaurants. My favorite pit stop is Lost Larson – their cardamom buns sell out fast so if you’re a fan of those, go early!
A Bite at Big Jones
Big Jones is home to Southern comfort food and has been around since 2008. It consistently makes lists citing ‘the best fried chicken’ in Chicago and the U.S. All ingredients are sourced locally and the environment is ‘casual cozy.’
Catch a Show at the Chicago Magic Lounge
The Chicago Magic Lounge has been on my date night list forever! The vibe is speakeasy meets magic and you enter the Lounge through a 1940’s commercial laundry space. (Pro tip: go early for some pics here hehe).
You’ll need tickets ahead of time – the weekend Signature shows run out fast.
If you make it in, you’re in store for a tableside magic intro and delicious small bites before the main acts hit the stage.
Hotel Rec: If you’re interested in staying in Andersonville for your trip, I highly recommend The Guesthouse Hotel, a beautiful boutique hotel, central to the area and the abovementioned spots.
👉 Click here to check prices & availability
Day 3
Explore Chinatown
Ranked by TimeOut as one of the best Chinatowns in the USA, Chicago’s Chinatown is teeming with delicious bakeries, quaint teahouses, and beautiful communal spaces.
I recently reintroduced myself to the area with my sister and toddler and it has incredible views of the skyline from Ping Tom Memorial Park. It honestly feels like an unintentional Chicago secret.
We also tried so many pastries in our latest visit – our favorite place for a signature custard bun has become Saint Anna Bakery.
Try this for your morning in Chinatown:
Start the day with a dim sum brunch in Old Chinatown before strolling over to New Chinatown and Saint Anna, maybe stopping at the Park or the Chinese American Museum of Chicago along the way.
Whatever order of events you decide, you’re in for a treat.
Insider Tip: Depending on where you’re staying, you can take the Chicago water taxi to Chinatown which is a unique local experience. I’d opt for the $20 all day pass because you can take the taxi to your next activity too.
Architecture River Cruise
Make your way over to the Riverwalk for the Architecture Cruise. I’ve done this tour three times now and I’d do it a fourth.
I thought it’d be a spew of boring facts. But really, it’s interesting history overlaid with real live stunning views of Chicago buildings. The tour brings the city together into one cohesive unit.
It’s another one of those activities that I’m quick to recommend to out-of-towners.
Dinner at a Top West Loop Restaurant
If you’re one for a nice meal, West Loop is a must during your time in Chicago. It’s essentially become the spot for all of Chicago’s hottest restaurants.
My favorites are the Croatian-Italian fusion restaurant, Rose Mary, and the Italian eatery, Monteverde. If you can’t reserve a table at either of these, try Au Cheval for a renowned burger or La Josie for some tacos and a platter of straight up vibe.
Other Restaurants Worth Mentioning:
- Giordano’s – My favorite deep dish if you’re up for trying it!
- Duck Duck Goat
- Time Out Chicago for a little taste of everything
- Tango Sur Argentinian Steakhouse*
- MIchael Jordan Steakhouse*
*These two are located outside of the West Loop
Rooftop Movie at Emily Hotel
Close out your evening with a rooftop movie at The Emily Hotel. If weather allows, this outdoor movie viewing spot is a can’t miss. They play a mix of classics and newer movies. You’ll need to reserve your tickets ahead of time.
Hotel Rec: The Emily Hotel is right in the West Loop and is another great accommodation option to consider.
👉 Click here to check prices & availability
Day 4
Enjoy your Hotel
If you haven’t had a chance to yet, opt for a lazy morning in and enjoy some of your hotel amenities. Every place I’ve recommended in this guide, and virtually anywhere else you might be staying in the city, offers something special.
Get a Prenatal Massage
Urban Oasis in Lincoln Park and lillieAnn’s in West Loop both offer fantastic prenatal massages. After a few days of exploring the city, I highly recommend a restorative massage for the perfect wind down.
Willis Tower Skydeck
To round out your trip and scratch any last tourist itch you might have, consider a visit to the Willis Tower Skydeck.
The Willis Tower, originally known as the Sears Tower (will Forever be the Sears tower to me!), is one of the tallest buildings in the world. The building includes a skydeck with a glass ledge (i.e., The Ledge) so that you can stand over the city while on glass.
Yea, I’m not trying that because of my fear of heights but if you’re into it, head over before you head home.
Where to Stay for a Babymoon in Chicago
If you’ve begun to research accommodations in Chicago at all, you know that there are plenty of options. Below are some of my top recommendations:
Luxury Hotel Rec: The Gwen on Michigan Avenue
The Gwen is peak luxury. It’s located on Michigan Avenue and has beautiful suites as well as a rooftop glamping option. Check it out if high-end is the feel you’re going for on your trip.
Click here to check prices & availability
Mid-Range Hotel Rec: The Hoxton
The Hoxton has a beautiful rooftop pool and snug, cozy rooms. It’s located in the heart of the West Loop, in the same building as two amazing restaurants: Cabra and Cira.
Pro Tip: I’ve noticed prices fluctuate more than usual for this hotel. If you see it available for under $300/night, I’d jump on that deal!
Click here to check prices & availability
Budget Hotel Rec: Fairfield Inn & Suites Chicago Downtown/River North
This Fairfield Inn is in the heart of the city and central to wherever you’d like to venture. It’s no frills but still has a modern and comfortable vibe.
Click here to check prices & availability
Insider Tips for Enjoying a Chicago Babymoon
Looking for a few more notes to make sure your trip goes sans hiccup? Pause to read my insider tips below:
- Out of all of the shows I’ve recommended, I’d prioritize a Second City show – Chicago is the birthplace of improv so this is a can’t miss!
- To get around, plan to rely on Chicago’s solid public transportation system and rideshares. A car of your own will be more of a hassle, especially if you’re staying in the city center.
- When there’s a choice in your route, opt for buses over the “L” (i.e., the Chicago train system). Buses are safer and offer more scenic routes.
- As with any big city, be aware of your surroundings and belongings (consider tucking your phone away rather than leaving it on the table when having dinner al fresco).
FAQ: Planning a Chicago Babymoon
Now that we have the ‘what to do’ part down, let’s dive into the FAQ to answer any last babymoon questions you have.
When should you go on a babymoon?
During your second trimester, somewhere between 4 and 6 months, is ideal. This is the time many women opt for since you’re mostly over your nausea. Medical professionals also cite the second trimester as the safest time to travel.
How many days do you need for a babymoon?
3 to 7 days is a good amount of time. That length ensures that the time you have is focused on you, your partner, and the adventure you’re about to begin together.
What is the point of a babymoon?
The point is to celebrate what is to come while also enjoying your last bit of one-on-one time with your partner. Take the time to sink into this fleeting phase you’re in and soak it all up!
Final Thoughts: The Perfect Chicago Babymoon
Feeling excited yet? As you can see, Chicago is bursting with fun things to do no matter what your interests are.
From the delectable food to the number of non-boozy options for entertainment that exist, I’d argue that Chicago is one of the best locations for a babymoon.
Cheers to you and crafting the perfect Chicago babymoon!