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Organizing a girls trip to Chicago can be both exciting and intimidating. With so many possibilities for attractions, activities, and places to stay, it can be challenging to decide what to do in a short amount of time.
I got you! In this post, I’ll give you ideas for how to plan the perfect girls getaway to the Windy City without breaking the bank. With a little bit of research and planning you’ll have the info you need to have a kick-ass girls trip to Chicago!
Photo byGenni Franklin
Is 3 days enough to visit Chicago?
Yes, if play your cards right, 3 days is enough to visit Chicago. There is so much to see in the city, from the iconic landmarks and museums to the delicious food and nightlife.
3 days is just enough time to be able to take in all the sights and sounds that Chicago has to offer. You can visit multiple attractions in a day, such as the Navy Pier, and take a cruise tour of the Chicago city architecture, or explore a different area of the city each day.
Is Chicago a good weekend getaway?
Absolutely! Chicago is the perfect weekend getaway because you can have a jam-packed itinerary without it feeling too rushed. In just a few days, you can explore the city’s rich cultural and historical heritage, enjoy the vibrant nightlife, or sample some of the city’s famed cuisine.
Plus, there’s plenty to do that won’t break the bank, and you may even find some deals on hotels and attractions.
What month is best to go to Chicago?
The best time to visit Chicago depends on what you’re looking to do during your visit. For the warmest weather, visit in July or August, and if you’re looking for festivals and outdoor activities, springtime is the best time for that.
If you’re on a budget, the months of April and October offer more affordable accommodations. Chicago is a great city to visit any time of year, so the best time to go depends on what you want to do!
What is the cheapest time to visit Chicago?
The cheapest time to visit Chicago is typically in the winter months, from December to February. Hotel prices and airfare tend to be lower during this time, and you can often find great deals on attractions. Of course, keep in mind it can get pretty cold and rainy (and windy lol) so you’ll want to keep this in mind when you’re deciding on what month to visit Chicago.
Setting a Budget for Your Girls Trip to Chicago
Establishing a budget is the first step to planning a successful girls trip to Chicago. Before you start booking accommodations and planning activities, decide how much you are willing to spend on your trip. Consider how many people are coming, how long you plan on staying, and the type of activities you would like to do.
If you’d like more resources check out these posts – how to plan a weekend trip on a budget and ways to save money for your next vacation.
Photo byGenni Franklin
Finding Affordable Accommodations for Your Girls Trip to Chicago
When planning a girls trip to Chicago, finding affordable accommodations can be a challenge. However, with a little research and flexibility, you can find a comfortable place to stay that fits your budget.
Ultimately, deciding on the right accommodations will depend on your budget, what type of experience you are looking for, and how many people are in your group.
Here are some tips on how to book affording accommodations in Chicago:
Consider alternative options: Instead of booking a hotel, consider alternative options like Airbnb or vacation rentals. These options often provide more space and a more authentic local experience at a fraction of the cost.
Book in advance and have flexible dates: By keeping your dates flexible and booking in advance, you can take advantage of early booking discounts and avoid peak season price hikes.
Look for deals and discounts: Check websites like Groupon, CozyCozy, Kayak, Travel Zoo, and Hotwire for deals and discounts on hotels, Airbnb rentals, and vacation rentals.
Opt for a less central location: Hotels in central locations like the Loop and Magnificent Mile can be expensive. Consider staying in a less central location, like Pilsen or Rogers Park, and using public transportation to get around.
Travel during off-peak times: Traveling during off-peak times, like weekdays or during the shoulder season, can result in lower hotel prices and fewer crowds.
Use Points and Miles to save money on accommodations: You cut down on your trip expenses significantly by redeeming points and miles for your accommodations. One of my favorite resources is The Points Guy beginners Guide.
I've also got some resources myself, grab a FREE Travel Hacking Beginner checklist at the bottom of this post.
Girls Trip Activities and Sightseeing
Planning activities for your girls trip to Chicago can be one of the most fun and rewarding parts of the trip. There are so many options for activities, from sightseeing and cultural experiences to shopping, festivals, and nightlife.
Activities and Guided Tours
Start planning by researching the different attractions and activities available in the city. Make a list of the attractions you and your group would like to visit and then look for discounts or deals that may be available.
If you plan on doing a lot of sightseeing, consider purchasing the CityPASS Chicago which will give you access to multiple attractions at a discounted rate.
There are also a ton of free things to do in Chicago, so you can alternate between paid and free activities to keep the budget in check.
Photo byGenni Franklin
Eating on a Budget
Chicago is known for its world-class cuisine, but dining out can quickly add up, especially on a girls trip. However, there are plenty of ways to enjoy the city’s delicious food without breaking the bank.
Here are some tips for eating on a budget in Chicago:
Look for daily specials: Many restaurants offer daily specials or happy hour deals that can help you save money while still enjoying a delicious meal and a vibey atmosphere.
Visit food halls and markets: Chicago is home to several food halls and markets, including the French Market, the Randolph Street Market, and the Lincoln Park Farmers Market.
Try street food: Chicago is famous for its street food, including its famous hot dogs, Italian beef sandwiches, and deep-dish pizza. These dishes are both delicious and budget-friendly, allowing you to try a variety of local favorites. And if you’re visiting during the summer months then you can take advantage of the Taste of Chicago food festival.
Explore ethnic neighborhoods: Chicago is home to a diverse array of ethnic neighborhoods, each offering its own unique cuisine at affordable prices. Head to neighborhoods like Pilsen for Mexican food, Chinatown, or Little Italy.
Eat at local cafes and diners: For a quick and affordable meal, try one of the city’s many local cafes and diners. These spots often offer classic American breakfast dishes, sandwiches, and salads at affordable prices.
Don’t forget to look for grocery stores and markets where you can pick up snacks and ingredients for a DIY meal or picnic. There are many beautiful parks in the city where you can post up with a glass of wine and enjoy the scenery.
Photo byGenni Franklin
Chicago Nightlife for a Girls Trip
Chicago is known for its vibrant nightlife scene, offering a wide range of options for a fun night out with the girls. From trendy rooftop bars to intimate jazz clubs, there’s something for every girl in your group.
Visit rooftop bars: Chicago is famous for its rooftop bars, offering breathtaking views of the city while you enjoy a drink or two. Popular options include the Signature Lounge on the 96th floor of the John Hancock Center, and Cindy’s Rooftop on Michigan Ave.
Explore the music scene: Chicago is home to a thriving music scene, with jazz clubs, blues bars, and live music venues offering a range of musical experiences. Check out venues like the Green Mill Jazz Club, Buddy Guy’s Legends, and the Jazz Showcase.
Try the craft cocktail scene: Chicago is home to a thriving craft cocktail scene, with bartenders pushing the boundaries of mixology to create innovative and delicious drinks. Head to bars like:
Enjoy a night of comedy: For a night of laughs, check out one of Chicago’s famous comedy clubs, such as Second City, Zanies, or The Laugh Factory.
Take in a show: Chicago is known for its thriving theater scene, offering everything from Broadway musicals to experimental plays.
Transportation Options
When it comes to transportation, you should consider taking public transportation instead of renting a car. Not only is it more affordable, but it can also be more convenient, as you don’t have to worry about parking or traffic.
Hop-on-Hop-off Bus Tours: One of my favorite ways to get around a new city is to purchase tickets for a Big Bus Chicago tour. Not only will you get a narrated tour, but you’ll get a ride around the city as well!
Public Transportation: The Chicago Transit Authority (CTA) operates an extensive network of buses and elevated trains, known as the “L,” throughout the city. It’s an easy and convenient way to get around.
Divvy Bikes: Chicago’s bike-share program, Divvy, offers a convenient and budget-friendly way to get around the city. You just rent a bike at one of the hundreds of stations around the city and drop it off at another when you’re done.
Taxis and rideshare services: Taxis and rideshare services like Uber and Lyft are readily available in Chicago and can be a convenient way to get around, especially if you’re traveling in a group. Be sure to compare prices and consider surge pricing during busy times.
Walking and cycling: Chicago is a very walkable city, with many of its top attractions located within close proximity to each other. The city is also known for its lakefront path and many parks, making it a great place to cycle.
Water Taxis: For a unique transportation experience, consider taking one of the city’s water taxis along the Chicago River. This is a fun and budget-friendly way to see the city’s skyline.
Girls trip to Chicago
Now that you know everything there is to know about planning a girls trip to Chicago, it’s time to get excited! Once you’ve narrowed down the activities and accommodations to fit your budget and schedule, you can start booking travel itineraries and booking flights!
Before booking flights you’ll want to read this post on big mistakes to avoid when booking flights.
You also have plenty of options when it comes to getting around. Even if you’re not comfortable navigating public transit, you can get around the city on foot with a map and guidebook in hand.
When you’re done with your trip, you’ll have memories that you can cherish for years to come, and hopefully some extra cash to spend on the next girls trip destination!