Girls Weekend in Chicago: The Ultimate 2-Day Itinerary
What do you get when you combine the best of Chicago with a group of fabulous women? A girls’ weekend in Chicago that is just as much fun as it is relaxing.
I’ve visited Chicago many different times with my sisters and friends, and let me tell you, it’s the ultimate destination for a girls’ trip.
Chicago is the kind of city that makes a long weekend feel easy.
You can walk almost everywhere, eat incredibly well, and still have time to slow down and enjoy it. There’s just enough to do without turning your trip into a checklist.
If you’re planning a girls’ weekend in Chicago, this is exactly how I would spend two days.
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Day 1: Riverwalk, City Icons, and a Classic Chicago Night
Start your first morning along the Chicago Riverwalk.
It’s one of the best introductions to the city. Grab a coffee and take your time walking along the water. The architecture alone makes it worth your time, even if you’re not usually someone who notices that kind of thing.
There are several boat tours that board along the river. I highly recommend the Chicago River Boat Architecture tour.
The ninety-minute tour is a fascinating journey along the Chicago River, offering a scenic view of one of America’s most iconic cities.
After that, head over to Millennium Park to see The Bean.
Officially called Cloud Gate, this mirrored sculpture is one of Chicago’s most recognizable landmarks. It reflects the skyline and the people around it, which makes it a fun (and slightly addictive) photo stop.
It’s popular, but it’s one of those places that still feels worth it once you’re there. Go earlier in the day if you can, before the crowds build.
While you’re in the area, it’s worth spending a little extra time in Millennium Park instead of just stopping for a quick photo. You can find more to do in this area in my post, Top Things to Do in Chicago for First Timers.
Spend your afternoon shopping the Magnificent Mile, relaxing, or just wandering through downtown.
For dinner, plan ahead and try Lou Malnati’s or Giordano’s for Chicago-style deep-dish pizza. It’s not a quick meal, and that’s part of the experience. Order early, settle in, and treat it like an event rather than just dinner.
Afterward, end the night with a rooftop drink. Chicago does rooftop bars very well, and tonight is the time to take advantage of it.
I love Cindy’s Rooftop for great views overlooking Millennium Park and the lake, and LondonHouse Rooftop for one of the best skyline views in the city.
Day 2: Brunch, Lake Views, and One Last Experience
Start your second day with brunch. Chicago has amazing food, and this is your time to slow down, catch up, and enjoy it.
So many brunch spots are in the River North area or near the Magnificent Mile. Check out The Beatrix River North or The Dearborn for two easy-to-reach spots with elevated menus.
After brunch, plan to spend part of your afternoon at one of Chicago’s museums. The Art Institute of Chicago, the Field Museum, and the Shedd Aquarium are some of my favorites.
If you’d rather be outside or want something a little more relaxed, the Lincoln Park Zoo is a free and scenic option just outside downtown. It’s set in a beautiful park and offers a quieter break from the busier parts of the city.
From there, head toward Navy Pier for spectacular views of Lake Michigan and the skyline. You don’t need much time here, so plan on about an hour to walk around and take it all in.
End Your Weekend Trip to Chicago with a Spectacular View
Before wrapping up your ladies’ trip, make time for one of Chicago’s observation decks.
You have two great options, the Skydeck Chicago and 360 Chicago.
The Skydeck, inside the Willis Tower, formerly the Sears Tower, is the highest observation deck in the U.S. and is known for The Ledge, where you can step out onto a glass platform 103 floors above the city.
360 Chicago in the John Hancock Building is slightly lower but offers incredible lakefront views and a more relaxed experience with the option to add the TILT thrill feature.
If you’re deciding between the two, Skydeck Chicago feels more iconic, while 360 Chicago includes a view of the Sears Tower.
Either way, it’s a memorable way to end your weekend.
Save Money with the Chicago CityPASS
If you’re planning to visit a few attractions, the Chicago CityPASS can save you money.
It bundles admission to several of the city’s top experiences and can save you up to 50% compared to buying tickets separately.
The Chicago CityPASS typically includes the Skydeck Chicago, 360 Chicago, and your choice of attractions, including museums and a river cruise.
It’s valid for several days, so it works well for a long weekend and takes some of the planning off your plate.
How to Get Around Chicago
Flying into Chicago is a breeze. The city has two major airports: O’Hare International (ORD) and Midway (MDW).
Both airports offer plenty of direct flights. Depending on where you’re flying from, you can often find reasonable fares.
I usually fly into Midway for my trips because Southwest Airlines flies directly from my home airport.
Once you’re there, Chicago’s public transit makes getting around so easy.
Grab a Ventra card to hop on the “L” (Chicago’s subway system), buses, or even trains to the suburbs.
Ride-share services like Uber and Lyft are excellent, especially if you’re heading out at night or unfamiliar with public transportation.
Pro tip: If you’re staying downtown, you’ll rarely need a car. Everything’s walkable, and the sidewalks are so scenic you’ll want to take your time soaking in the sights.
Best Time to Visit Chicago
For the best experience, travel to Chicago in the spring or summer. The weather is beautiful, the attractions are active, and the city is alive.
No matter when you go, you will have a fantastic time in this beautiful city on your Chicago girls’ getaway.
Where to Stay in Chicago for a Girls Trip
For a girls’ weekend, you want something central, walkable, and close to restaurants and things to do. The good news is that Chicago makes that pretty simple if you pick the right area.
I’d focus on three central areas.
River North is the best overall choice, especially for a first visit, because you’re within walking distance of the Riverwalk, restaurants, and most of the places you’ll want to see.
The Magnificent Mile is another solid option if shopping is part of your plan and you want something straightforward and convenient.
If your group tends to plan trips around meals, the West Loop has some of the best restaurants in the city and a slightly trendier, more local feel.
I’ve personally stayed at the following hotels and would stay at any one of them again:
Ready to Plan Your Girls’ Trip to Chicago?
Chicago is truly a gem for a fabulous girls’ weekend!
Whether exploring iconic attractions like Millennium Park and Navy Pier on a mother-daughter weekend or indulging in retail therapy with friends along the Magnificent Mile, Chicago never disappoints.
The memories made here, strolling along the lakeshore or enjoying drinks at one of its lively rooftop bars, are unforgettable.
Don’t wait any longer.
Book your tickets, plan your itinerary, and let Chicago be the backdrop to your next amazing girls’ trip.
The experiences awaiting you in this dynamic city will create bonds and stories that will last a lifetime.
Start planning using this travel guide now, and prepare to make memories that will have you smiling for years to come!
