The Ultimate 4-Day Chicago Bachelorette Party Itinerary: Your Complete Guide
Trip Length: 4 Days, 3 Nights | Group Vibe: Adaptable to All Personalities | Budget Range: $500-2,500 per person
Planning a Chicago bachelorette party? We've got you covered with an itinerary that actually works for real friend groups- no stress, no outfit drama, just good vibes and incredible memories. Whether you're the MOH trying to nail the perfect weekend or a bride wanting to give your girls the best time, this guide has everything you need for an unforgettable 4-day celebration in the Windy City.
📌 If you’re looking for hotel, restaurant, and activity lists to build your own schedule, head to our full Chicago Bachelorette Planning Guide instead.
Day-by-Day Itinerary
Day 1: Arrival, Riverwalk, Sunset Rooftop, Dinner
Morning/Afternoon: Arrival & Check-In
- 10:00am - 3:00pm: arrivals and hotel check-in window (River North or West Loop base suggested): if rooms are not ready, store bags with the front desk and start here.
Most of your group will arrive throughout the day, so plan a flexible check-in window. If your accommodation isn't ready, use this time for a casual lunch and initial bonding.
👚 Union Threads outfit focus: Start your weekend in our classic crewneck sweatshirt. It's travel friendly, effortlessly chic, and perfect for moving from airport to Rivverwalk. The relaxed fit looks intentional in photos, and the soft cotton blend feels great after traveling.
Late Afternoon
- 3:30pm - 4:45 pm: Chicago Riverwalk stroll: Grab a first round at City Winery Riverwalk. This is a low-lift meet-up that works even if flights are staggered. If rooms aren't ready, store bags and start here.
Location: Start at Michigan Avenue Bridge, walk east to Lake Shore Drive.
Why it's perfect for Day 1: This gentle 1.5-mile walk along the Chicago River gives everyone a chance to stretch their legs, chat, and get gorgeous city photos without pressure. The vendors along the way offer snacks and drinks, and there are plenty of spots to sit and catch up.
Weather considerations: If it's cold (November-March), limit this to 30 minutes and focus on the portion near Michigan Avenue with more indoor warming options.
Evening
- 5:15pm - 6:45pm: Sunset Round at Cindy's Rooftop (Loop): Book the table 60–90 minutes before sunset for the best light and photos.
- 7:15pm - 9:00pm: Dinner at Quartino (River North): Everything is designed for sharing, from the charcuterie boards to the pasta dishes. The lively atmosphere handles big groups beautifully, and the affordable prices mean no one's stressing about money on the first night. Make reservations for groups of 8+ through OpenTable. ask about large-party policies (8+).
- Dinner Alternative: Irazu (Bucktown): This Costa Rican gem offers a warm, hospitable environment perfect for groups. The portions are generous, perfect for sharing, and the prices are incredibly reasonable. Don't miss the oatmeal milkshake!
night
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9:15 pm - late: Choose your vibe in River North.
Party pick: Howl at the Moon (dueling pianos).
Cocktail warm-up: The Berkshire Room.
- Day 1 recommendation: Hotel bar or nearby casual spot for those who want to continue the night. Keep it low-pressure since everyone's traveled and you have big days ahead.
- For the introvert: Day 1 is intentionally low-key to help everyone ease into the group dynamic. If you need recovery time, use the 2-hour window between the Riverwalk and dinner to rest at the hotel. The dinner spots we've chosen are conversational, not club-loud.
- Budget note: $$ to $$$ depending on rooftop and drinks.
- Logistics: Riverwalk and Quartino are walkable if you are based in River North. Cindy's is a short rideshare from Quartino. plan 10–15 minutes for each hop.
- Weather swap (rain plan): if rooftop is rained out, do a later round at The Berkshire Room and save Cindy's for tomorrow.
Day 2: Chicago Signature Experiences
Morning
- 9:00am - 9:40am: Millennium Park photos at Cloud Gate before crowds. this puts you close to the cruise dock.
- 10:00am - 11:30 am: CAC Architecture River Cruise aboard First Lady: Arrive 30 minutes early at 112 E Wacker Drive for boarding. The dock has stairs and ramps; request assistance if needed.
Booking tip: Reserve online in advance, especially for weekend morning slots. They offer group discounts for parties of 10 or more.
Afternoon
- 12:00pm - 1:30 pm: Lunch at River Roast (River North): It is a short walk from the dock and works well for mixed tastes.
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1:45pm - 4:30pm: Afternoon Activity:
- Option A: Hotel reset: Use this buffer for rest, outfits, and glam. It keeps energy high for the evening.
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Option B:Classic Chicago sightseeing
Must-see: Cloud Gate ("the bean"), Crown Fountain, and Lurie Garden.
Shopping: walk north on Michigan Avenue for the Magnificent Mile experience.
Time management: plan a full hour at Millennium Park for photos and exploration, then 1.5 hours for shopping and browsing.
If you choose Option B, plan to leave Millennium Park by 5:45 pm and rideshare directly to Carnivale to stay on schedule.
Evening
- 6:30pm - 8:30 pm: Dinner at Carnivale (West Loop): Festive and group-friendly. +10–15 minutes for rideshare. Book through Tock for groups up to 10, or reserve one of their private spaces for larger parties. Ask about large-party policies (8+).
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9:30pm - late: Choose your night finish:
Views: LH Rooftop (Loop).
Party pick: Howl at the Moon (River North).
Club option: Joy District (River North) if you want a dance floor.
- Budget note: $$$ today with the cruise plus dinner and evening rounds.
- Logistics: Millennium Park to the cruise is a walk. Cruise to lunch is a walk. West Loop dinner requires a 10–15 minute rideshare. West Loop to LH Rooftop or River North is another short hop. pad 10–20 minutes for Saturday traffic.
- Weather swap (rain plan): trade the cruise for WNDR Museum or Color Factory, then keep lunch and dinner as planned.
Day 3: Peak Celebration Mode (Sunday)
Pick one of the two tracks below to minimize zig-zagging across the city:
Track A: West Loop Cluster
10:00am - 12:00pm: Brunch near Millennium Park at Wildberry, or book Aba for a rooftop brunch in Fulton Market. join the waitlist early if needed.
12:45pm - 2:15pm: Color Factory (Fulton Market) or
2:00pm - 3:30pm: WNDR Museum (West Loop). both are timed-entry and photo-friendly.
4:30pm - 6:00pm: Aire Ancient Baths (River West). book treatments in advance and keep this as a quiet reset.
6:30pm - 8:00pm: Easy dinner at Time Out Market Chicago (Fulton Market), so everyone can grab what they want.
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8:30 pm - late, choose one nearby:
Lazy Bird (cocktails, live music)
Kumiko (cocktail temple)
Raised (views) / I|O Godfrey (views, large groups)
Howl at the Moon (party pick)
Joy District (club)
Sidetrack (LGBTQ anchor)
- Budget note: $$ to $$$ depending on museum tickets and spa choices.
- Logistics: All stops are short rides or longer but doable walks within Fulton Market, West Loop, and River West. Plan 10–15 minutes per hop.
- Weather swap (rain plan): If rain hits, keep this track as is. Both attractions are indoors.
Track B: Beach Day + Uptown Evening
10:00am - 11:30am: Brunch closer to the lake. The Bongo Room in Wicker Park works well before a beach day, or choose a Lincoln Park café.
12:15pm - 3:30pm: North Avenue Beach cabana at Shore Club or Castaways. build in sunscreen and water breaks.
4:15pm - 5:15pm: Optional hotel reset.
6:00pm - 8:00pm: Casual dinner near the lake or back in River North.
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8:30pm - late: choose one nearby
Rooftop near the park: The J. Parker at Hotel Lincoln for lake and skyline views.
Speakeasy vibe in Wicker Park: Bordel for live jazz, cabaret, or DJs.
Cocktail lounge in River North: The Berkshire Room for dealer's choice cocktails.
Party and club picks in River North: Electric Hotel or Sound-Bar for a high energy finish.
LGBTQ anchors in Lakeview: Sidetrack or Roscoe's Tavern for theme nights and dancing.
- Budget note: $$ today, rising to $$$ if you reserve a cabana.
- Logistics: Wicker Park to North Avenue Beach is a rideshare of about 15–25 minutes. beach to River North or the Loop varies by traffic. if you plan Aire Ancient Baths, consider moving it to Monday morning to avoid a long beach to River West ride.
- Weather swap (rain plan): if the beach is not viable, pivot to the West Loop track above.
Day 4: Departure & farewell
Path A: Spa morning, simple send-off
9:00am - 10:30am: Optional Aire Ancient Baths if you moved it from Sunday.
10:30am - 12:00pm: Coffee and light bites near your hotel. Take last photos along the Riverwalk.
12:00pm - 3:00pm: Departures. Request late checkout on one room if possible.
or
Path B: Farewell brunch + quick final activity
9:00am - 11:00am: Farewell brunch at The Bongo Room (1470 N Milwaukee Ave). plan for $12–$20 per person. cozy, generous portions, linger-friendly.
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11:30am - 1:00pm: Choose one
Chicago Pedway stroll near the Loop for an easy, weatherproof walk, or
Garfield Park Conservatory for a calm, photo-worthy close.
1:00pm - 6:00pm: Staggered departures. Hotels can store luggage for late flights.
- Budget note: $ to $$ today.
- Logistics: keep moves tight. store bags at the hotel. allow 45–60 minutes to ORD on the Blue Line or 30–45 minutes to MDW on the Orange Line; rideshare times vary with traffic. pick the path that stays closest to your hotel and flight window.
- Not everyone will leave at the same time, so plan for staggered goodbyes. Those staying longer can explore Oak Street Beach or do last-minute shopping on Michigan Avenue. Hotels can store luggage for late departures.
- Transportation to airports: O'Hare (ORD): CTA Blue Line ~45–60 minutes ($5) or rideshare ~$35–$50. Midway (MDW): CTA Orange Line ~30–45 minutes ($2.50) or rideshare ~$25–$35.
- Departure Day Success Tips: Book late checkout for at least one room to serve as a "headquarters" for luggage storage and final preparations. Create a group chat specifically for departure logistics, and designate someone to coordinate rideshares to the airport.
Reservation And Timing Notes
- Book early: Cindy's Rooftop, LH Rooftop, Quartino, Carnivale, and Howl at the Moon table packages are in demand on weekends. Reserve 2 to 4 weeks ahead in peak months.
Sunset timing: Schedule Cindy's for 60–90 minutes before sunset to catch the light and a relaxed round before dinner.
Buffers: add 15–30 minutes before the river cruise for check-in and boarding, and another 15 minutes before Saturday dinner for rideshare and outfit changes.
Dress codes: several rooftops and clubs lean smart casual. Comfortable shoes are best for the Riverwalk and museum time. Bring a light layer for evening wind.
Transport: walk or take transit by day, where it is simple. At night, use a rideshare. plan shared pickup points at Cindy's, Quartino, Carnivale, and your hotel to keep the group together.
Accessibility: the Riverwalk and major museums have accessible routes. Confirm accessibility notes for rooftops and boats when you book.
Pro Tips for Group Success
Managing Group Dynamics Over 4 Days
Let's be real - even the best friend groups can have moments of tension during an extended celebration. Here's how to navigate them:
Build in alone time: Schedule 1-2 hours of free time each day for people to rest, shop, or recharge solo.
Flexible participation: Make most activities optional. Not everyone needs to do everything together.
Budget check-ins: Have honest conversations about spending before each expensive activity.
Energy management: Plan one high-energy and one chill activity each day to accommodate different energy levels.
Conflict resolution: Designate someone (usually the MOH) to mediate if tensions arise.
Chicago-Specific Considerations
Transportation: The CTA (public transit system) is reliable and affordable, but rideshares (Uber/Lyft) are worth it for late nights, carrying luggage, or when time is of the essence.
Neighborhoods: Each neighborhood has its own vibe. River North is central and touristy, Wicker Park is trendy and artsy, Lincoln Park is upscale and family-friendly.
Tipping: Chicago service workers appreciate good tips. Standard is 20% for restaurants, $1-2 per drink at bars.
Weather apps: Download a reliable weather app. Chicago weather can change quickly, especially in spring and fall.
Final Thoughts
The key to a successful 4-day celebration is balance: high-energy moments and chill recovery time, splurge experiences and budget-friendly fun, group activities and individual space.
Remember, the best bachelorette parties aren't about perfect Instagram moments (though Chicago definitely provides those). They're about celebrating the bride in a way that feels authentic to your group. Whether you're architecture enthusiasts, food lovers, nightlife queens, or a mix of everything, Chicago has something special waiting for you.
Ready to look amazing throughout your 4-day Chicago adventure? Check out our full collection of bachelorette-worthy pieces at Union Threads. Because you deserve to feel confident and comfortable while creating memories that will last a lifetime.
Free Resources to make planning even easier
Want to make this even easier? We've created some planning tools specifically for you:
Chicago Bachelorette Planning Guide: For the complete breakdown of Chicago neighborhoods, safety, budget, and full activities and restaurants list, check out the full planning guide.
Group Coordination Survey Template: Anonymous survey to get real budget and activity preferences.
Bachelorette Packing Checklist: What to bring for mountain weather and activities.
Bachelorette Invitation & Itinerary Templates: All the important information for your group in one place.
The Best Bachelorette Party Games: Easy and fun games everyone in your group will love.
Questions about planning your Chicago bachelorette party or finding the perfect coordinated pieces for your group? Drop us a line - we love helping make these celebrations as special as they deserve to be.
