Top Chicago Bachelorette Party Ideas for Winter: Inside Look at My Snow in Love Celebration
If you’re headed to the Windy City for your bachelorette party, here is your ultimate party planning guide to the perfect girls weekend!
From the best places to eat & stay, parking tips, weekend itinerary suggestions, girly & aesthetic brunch locations, indoor activities for winter (or bad weather), planning advice, gifts for bridesmaids, decor inspiration, bride & bridesmaid outfit ideas, and helpful budgeting tips to keep costs low, we’re covering it all!
Chicago Bachelorette Party Ideas for Winter
We just got back from my bachelorette party a few weeks ago and it was absolutely PERFECT. I’m excited to recap it with you and share all our photos! Keep reading for all our Chicago bachelorette party ideas.
Shop Chicago Bachelorette Party Ideas – Decor, Outfits & Gifts
Choosing a Bachelorette Location & Theme
Since my wedding is in May (in the Midwest), I knew it was likely that whenever I had my bachelorette, the weather would be cold. Unless, we traveled somewhere warm. But, I didn’t want the stress of traveling, plus I wanted to keep costs low for everyone.
When first brainstorming a destination for my bachelorette party, I knew I wanted to go somewhere within driving distance of Milwaukee and somewhere that had lots of winter/indoor activities.
Chicago is less than an hour and a half away from Milwaukee and has plenty of options when it comes to restaurants, group experiences, classes and activities, etc. so we knew we’d be able to find tons of things to do!
Embracing the cold weather here, we decided to go with the theme Snow in Love. I also happen to LOVE Beyoncé’s song Drunk in Love, so the theme was very fitting.
I also don’t know anyone personally that has done this theme before, so I thought it would be fun to do something different!
Keeping Costs Low
Like I mentioned before, I wanted to make this trip really affordable for all the bridesmaids. I didn’t want anyone to feel like they were stretching their budgets to come.
We decided on staying one night in Chicago. I felt like that would be the perfect amount of time for all the activities we wanted to do, but wouldn’t make us feel rushed.
Plus, with a group of 13, I felt like two nights could be a bit much.
Here are a few other ways we saved money to keep the entire trip under $200 per person.
- Booking parking ahead of time
- Choosing just 1-2 main activities for the trip
- Finding free things to do in the city (our itinerary is below)
- Packing group games to play
- Finding a reasonably priced hotel or Airbnb
I know Chicago is a traditionally expensive city, but it’s definitely possible to have a low-cost bachelorette party here!
Our Weekend Itinerary:
My incredible sister put together the most perfect bachelorette itinerary for us! The weekend was seriously SO much fun and I wish I could re-live it.
I’ll share our exact schedule and all the activities she planned for us below.
Ultimate Chicago Bachelorette Party Guide & Itinerary
Saturday, February 3rd
- Brunch at Blue Door Farm Stand – 10:30am
- Shopping in Lincoln Park (if there’s time before dance class)
- Dance Forever Cardio Dance Class – 2:00-3:30pm
- Hotel Check-in, Decorate Room & Freshen Up – 4:00-6:00pm
- Dinner at Lou Malnati’s – 6:30pm
- Ice Skating at Millennium Park – 9:00pm
- Hot Cocoa & Games at Hotel
- Late Night Swim at Hotel (if there’s time)
Sunday, February 4th
- Check out of hotel – 11:00am
- Brunch at Hampton Social River North – 11:30am
- Shopping along Michigan Avenue – 1:00pm
- Walk along Navy Pier (weather permitting)
- Drive Home
Restaurants to Eat At
Chicago is known for its incredible restaurant scene. There are seriously SO many restaurants to choose from, it’s crazy. It was hard to narrow down where we wanted to eat because every place looks delicious!
We landed on three restaurants that I’ll talk about below.
All three of these were able to reserve a table for us ahead of time and could accomodate large groups.
Just note that most do not allow you to split the check. Lou Malnati’s was the exception and allowed everyone to pay separately which made things so much easier!
Brunch at Blue Door Farm Stand
Blue Door Farm Stand, a farm to table cafe in the Lincoln Park neighborhood, was our first brunch spot of the day Saturday morning!
The restaurant is SO cute inside! It has a homey, yet elegant aesthetic to it and all of the food was really yummy!
I had the Buttermilk pancakes with whipped butter and maple syrup and oh my gosh, these were just incredible! Highly, highly recommend eating here with your group!
Dinner at Lou Malnati’s
Lou Malnati’s is my all time FAVORITE restaurant. Their buttery crust Chicago-style pizza is phenomenal, so I knew I wanted to eat here while we were in Chicago! We ate at the Lou Malnati’s on Michigan Ave, which was just a short walk from our hotel.
We ordered garlic bread and the Lou’s bruschetta to share, and then my sisters and I split a cheese deep-dish pizza. Everything was delicious!
Our waiter was so nice and even brought out Tiramisu with a candle on it for me because he knew we were celebrating my bachelorette.
Also, side note, deep-dish pizzas take around 30-40 minutes to make, so plan accordingly!
Brunch at Hampton Social – River North
I’ve actually eaten at the Chicago Streeterville location before for dinner. But, I’ve never been here for brunch, so I was super excited to try it out. I absolutely LOVED the Hampton Social!
This was definitely my favorite restaurant we ate at and my mom and sisters agreed.
The restaurant had a fun coastal vibe and there was live music! All the plates and napkins were blue and matched the nautical aesthetic and there was a large sitting area with couches and hammock chairs that you could hang out in.
The River North Hampton Social location was massive, making it the perfect spot for large groups and bachelorette parties!
And I can’t forget to talk about the delicious food! My sister and I ordered the Monkey Bread and Spinach dip to share. We ate all of it, it was so good. I would drive down to Chicago just to order the Monkey Bread again.
My mom and a few other girls ordered the Bananas Foster French Toast and also loved it!
Other restaurants we considered: Summer House, Wildberry Pancakes and Cafe, River North Bistro, Beatrix, 3 Arts Club Cafe, Cindy’s Rooftop
Where to Stay
We stayed at the Hilton Garden Inn Chicago Downtown/Magnificent Mile at 10 E Grand Avenue and I couldn’t recommend this hotel enough. My fiance and I have stayed here before and it’s just wonderful!
Exceptionally clean and well-kept, affordable, friendly staff, and lots of on-site amenities.
The hotel is located in River North, which is just a few blocks away from Michigan Avenue. The Bean and Millennium Park are a 15 minute walk away, and there are tons of restaurants, rooftop bars and shopping all around the hotel. Everything was so close we didn’t even have to Uber.
We stayed on the 23rd floor (the very top floor) in a suite and it was absolutely massive! There was a kitchen and living room area, one King size bed and a pull out couch, so four of us stayed in our room.
We also booked three other hotel rooms for the girls and all of the rooms had gorgeous views of the city!
If you’d like a connecting room, you can call the hotel after you book! That’s what we did, so that one of the rooms adjoined to ours.
Where to Park
We used Spot Hero (it’s a parking app) to pre-book all of our parking spots before we came to Chicago. I highly recommend doing this because downtown Chicago can get crazy, especially during rush hour.
Thankfully, driving in early Saturday Morning wasn’t terrible and leaving Sunday evening wasn’t bad either.
Really, we only hit traffic the last 15 miles into the city, and it wasn’t as bad as I was expecting. We booked two Spot Hero spots. The first one at 755 W North Avenue in Lincoln Park. This garage was within walking distance to both Blue Door Farm Stand and the Dance Forever studio.
Our second parking garage was actually connected to our hotel, which was SO convenient for carrying our bags and all of the decor/gifts. It was the North Bridge (10 E Grand Avenue) garage.
Both spots were very affordable, and allowed us to walk to all of our activities. This definitely saved us money on Ubers.
Things to Do in Chicago in Winter
Here’s the activities we did in Chicago in early February. You can still do most of these Chicago bachelorette party ideas in the Summer, just probably not outdoor ice skating haha!
Cardio Dance Class at Dance Forever
This was THE BEST PART of my bachelorette!! I LOVE to dance so I really wanted to find a fun dance studio in Chicago that would host a bachelorette party!
My sister did all the research and booked us a private dance class at Dance Forever, in Lincoln Park, Chicago.
We had all the girls wear black workout clothes and I wore white, which was surprisingly hard to shop for! There’s not many great quality white workout leggings LOL.
The class was SO FUN. Our instructor, Taylor, taught us a choreographed dance, and we basically danced it to all different songs! My sister had submitted song requests beforehand, so Taylor knew the type of music we liked.
We danced our hearts out to Beyonce, Britney, Miley, Demi, Taylor Swift.. All my favorites.
We popped champagne after, took photos, and they let us use the room after to continue dancing and talking! The studio also had a cute little dressing room area for us to change in too! I already can’t wait to go back here.
If you have a girls trip planned for Chicago, I highly recommend looking into taking a cardio dance class at this studio.
Ice Skating at Millennium Park
If you’ve never been ice skating at Millennium Park, definitely add this to your list of things to do while in Chicago. We had such a great time and it’s so pretty at night with all the city lights!
Admission is free for the ice rink if you have your own ice skates, but if you need to rent a pair it’s $20. And although the rink is free, you still have to reserve a time slot online for your group. This must be a newer policy because I’ve gone previously and never had to sign up beforehand.
We signed up for the 9-10:30pm time slot and it worked out great because the rink wasn’t super crowded!
Hot Cocoa & Games at Hotel
After skating, we walked back to our suite for a little pajama party with hot chocolate and games! I got matching dusty blue pajamas for the girls to wear so we could take some photos with all the decorations.
My mom and sister set up the cutest Hot Cocoa Bar with blue Snow in Love themed snacks and my sister even made a fun trivia game with 16 questions to see who knows me the best!
We packed a bunch of other group games to play, but by the end of the night we were absolutely exhausted from all our activities. So, we only managed to squeeze in one game of This, That and Everything before heading to bed.
It was so much fun just hanging out with all my best friends, talking, playing games, eating and taking photos. I can’t think of a more perfect way to end the day.
Other group games we love: Green Team Wins, The Game of Things, Scattergories, Tabletobics Conversation Starters (great way to get to know people)
Shopping along Michigan Avenue
After brunch at the Hampton Social on Sunday, we headed to Michigan Avenue to do some shopping. It’s always fun window-shopping and just looking in all of the stores!
I didn’t end up buying anything, but it’s such a fun shopping experience and so different from what we have in Wisconsin.
Here are a few of the many stores that you can shop at along Michigan Ave: Zara, ALO Yoga, UGG, Sephora, Aritzia, Nordstrom, Nike, Cartier, Saks Fifth Avenue, Loft, Marshall’s, Coach & so many more!
You can also stop in the five-story Starbuck’s Reserve Roastery, which is the largest Starbuck’s in the entire world.
Other Chicago Bachelorette Party Ideas: Spa day at AIRE Ancient Baths, wine tastings (Chicago Winery and Ella Elli) candle making class at Aura Candle Bar, take a cooking class at Eataly, scavenger hunts around the city (Maid of Honor could coordinate this), Broadway in Chicago
The Outfits
Day One Outfits – Brunch, Dance Class & Pajama Party
It was so much fun planning all of the outfits I was going to wear this weekend. I mean how often do you get to wear cute all white Bride attire!? One of my friends gifted me this Bride crewneck, so I paired it with these white joggers and my Nike sneakers for the drive down.
I had packed an outfit to change into for the first brunch spot, but decided to stay in my sweat set!
For the cardio dance class, I changed into a white workout set. My cropped workout tank is from Amazon – I own it in SO many colors. It’s a personal fave. For the girls, I had all of them wear black because I assumed everyone owned a pair of black leggings and a black top.
For dinner and ice skating, we just wore whatever we wanted to stay warm. I happened to have a cream Ralph Lauren coat that I absolutely love, so I wore that with a pair of black leggings and my Mrs. beanie. The girls wore whatever black or dark-colored coats they owned with their matching black hats!
Back at the hotel, I laid out a pair of blue satin pajamas from Kennedy Blue for our pajama party. These were SO cute for photos. Their website has tons of colors to choose from too!
Shop my Day 1 Outfits here:
Day Two Outfits – Brunch & Shopping
Finally, my last outfit, which I think was my favorite because I got to wear my pearl denim WIFEY jacket. I had on a white long sleeve bodysuit, these ankle straight Abercrombie jeans and wore the denim jacket over it.
The attire for brunch on Sunday was Blue Casual, so everyone else dressed in jeans and a blue button up or blouse.
Overall, I really wanted all the outfits to be comfortable, cute and easy for my bridesmaids to put together with clothes they already have in their closet!
Shop my Day 2 Outfit here:
Gifts for Bridesmaids
Obviously, I wanted to stick with the Snow in Love theme, so everything I got for my girls revolved around that. Since we were going ice skating, I thought it would be cute to get them matching rhinestone monogram black beanies and custom fuzzy socks.
Both of these were from Wedding Favorites! They have so many gifts, accessories and apparel for brides and bridesmaids. If you remember, this is where I got most of my Bridesmaid Proposal Gifts from! You can read more about all the gifts I gave my girls here.
I also thought it would be cute to include a monogram makeup bag (also from Wedding Favorites), and my favorite eye gels from Patchology.
For our pajama party, I found these cute matching Dusty Blue satin pajamas. These were really affordable and shipped within 3-5 business days!
I got my true size XS, but I would’ve also been fine sizing up to a Small. If you like your pajamas to fit a bit looser, definitely size up!
Bachelorette Planning Tips for a Stress-Free Weekend
I have to give a shout out to my wonderful maid of honor and sister for planning the most incredible bachelorette party weekend for me. I had such a good time with my closest friends!
To help anyone else planning a bachelorette party, I asked my sister to share her advice. So, here are some helpful bachelorette planning tips if you’re heading to Chicago soon!
1. Send out the itinerary ahead of time
This way everyone knows when and where to meet. My sister made this cute little graphic on Canva which laid out our entire itinerary for the weekend. It had all the activities listed out, the times of each activity, the addresses, and the attire.
Gabby sent it out via text to everyone beforehand, so that the girls could reference it throughout the weekend. It made our entire weekend run very smoothly!
2. Book parking spots ahead of time
You don’t want to have to worry about parking in a big city. It’s stressful and difficult. Trust us, just book all your parking ahead of time.
3. Give yourself more time than you think for every activity
Most of the time, acivities run longer than expected, especially with a large group of girls. Plan ahead and space your activities out so that you’re not rushing from thing to thing.
4. Make all reservations ahead of time
We highly, highly recommend making reservations ahead of time for all of the restaurants (and activities). For restaurants that didn’t take reservations, we just chose not to eat there because we didn’t want to risk not getting a table.
Also, for restaurants that you do reserve ahead of time, make sure you get a confirmation text. There was one restaurant we booked that didn’t send a text to confirm our reservation, and it turns out the reservation didn’t go through in their system.
We were able to get it fixed over the phone, but this goes to show, always confirm your reservation a few days before!!
5. Order decorations from Amazon!
My sister ordered all the decorations off Amazon and everything was really affordable!
For blowing up ballooons and setting up the decor, make sure you pack an electric air pump, a hand pump, scissors and tape. Masking tape worked fine for us, but blue painters tape works too!
Shop the Decor & Bridesmaids Gifts
6. Decide how to split the bills ahead of time
You can really do this however you want, but I’ll share what we did because it worked really well! After each meal, we passed around the receipt and had everyone initial what meals and drinks they had.
My sister kept track of all the receipts, and at the very end of the bachelorette, she made a spreadsheet of what everyone owes for each restaurant/activity.
This allowed my sister to calculate the tax and tip that everyone owed as well, so that no one was stuck paying more than they owed. It really made things easy and stress-free throughout the weekend.
7. Create an outfit inspiration collage on Canva
If you have any themes or specific outfits/colors you want the bridesmaids to wear, it’s really helpful to create a outfit inspiration board either on Canva or Pinterest. This way, the bridesmaids can get an idea of what they should wear for each activity!
I think this wraps up all my Chicago bachelorette party ideas & planning tips! I really hope this post was helpful for any Brides or Maids of Honor planning a bachelorette party.
There’s so much that goes into planning a trip like this, but it’s so worth it. I hope you have the absolute best time on your bachelorette trip!
Shop Everything from this Chicago Bachelorette Party Ideas post
Other posts you may like:
- Bridal Shower Prize Basket Ideas Your Guests Will Love!
- Bridesmaid Proposal Box Ideas: Everything I Gave My Girls
- 25+ Thoughtful Gift Ideas for the Bride to Be
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