Everything You Need to Know About Chicago's Literary Scene (and beyond)
Chicago is a city that never runs out of surprises. From its vibrant literary scene to its ever-changing seasonal activities, there’s always something new to discover, whether you’re a lifelong local or a first-time visitor. Over the years, I’ve had the joy of exploring and sharing my favorite spots in this dynamic city—whether it’s the best local bookstores, hidden gems for family outings, or curated travel itineraries for enjoying Chicago like a tourist and a local all at once.
In this post, I’m rounding up a collection of my most-loved Chicago-centric blog posts, offering everything from inspiration for family-friendly adventures to suggestions for seasonal must-do activities. Plus, if you’re a book lover or just looking to explore the city’s literary side, I’ve got plenty of recommendations for that too. So whether you’re planning a weekend getaway, a day of family fun, or simply looking for ideas to experience the magic of each Chicago season, you’ll find all the inspiration you need right here. Ready to dive into the Windy City’s best offerings? Let’s get started!
I want to note that I do not get paid to do these posts, I just love authors and the book industry. However, they do take time and energy to create. If you want to donate a few dollars to my coffee fund, which keeps this blog going, you can do so here: https://venmo.com/AshleyHasty or here: http://paypal.me/hastybooklist.
Everything You Need to Know About Chicago's Literary Scene (and beyond)
Books Set in Chicago
Looking for your next great read with a strong sense of place? Discover stories where Chicago isn’t just the setting—it’s the heartbeat. From sweeping love stories and gritty thrillers to powerful historical fiction and unforgettable memoirs, these books capture the spirit of the Windy City in all its glory. Whether you're a local or just love a good city-centric read, this list will transport you straight to the streets of Chicago—no plane ticket required.
Chicago Authors You Should Know
From iconic literary legends to rising stars on the indie scene, Chicago is bursting with authorial talent. In this post, we’re spotlighting the writers who live and work in the Windy City—crafting unforgettable characters, penning page-turning plots, and drawing inspiration from the neighborhoods, lake views, and rich history that make Chicago so unique. Whether you're looking to add a new name to your reading list or hoping to support local voices, these Chicago-based authors are ones to watch.
Chicago Book Events and Festivals You Won’t Want to Miss
Chicago's literary scene is buzzing with book festivals, author events, and even dog-friendly fundraisers you won’t want to miss. Whether you're browsing indie bookstore pop-ups, attending a panel at Printers Row Lit Fest, or cheering on pups for a great cause at Bark 'N Ball, there’s something magical happening year-round. Dive into this guide to the best Chicago book events and start planning your next literary outing!
Chicago Literary Landmarks Every Book Lover Should Visit
Whether you're sipping a cocktail in a library-themed lounge, tracing the footsteps of literary greats like Hemingway and Hansberry, or wandering the aisles of one of the city's beloved indie bookstores, Chicago is a haven for book lovers. This guide uncovers the city’s most charming literary landmarks, cozy reading nooks, and bookish spots to dine and drink—perfect for locals and visitors alike who want to add a little literary magic to their Windy City adventures.
Local Chicago Bookstores
Chicago is a city of neighborhoods—and each one seems to have its own beloved bookstore tucked into a cozy corner. Whether you're after a carefully curated indie selection, a bustling shop with staff picks galore, or a hidden gem where you can sip coffee between chapters, this list has something for every kind of reader. Come wander the stacks with me as we explore the most charming, quirky, and must-visit bookstores across the city.
Chicago with Kids
What to do in Chicago with Kids
Planning a family getaway? Discover why Chicago is the perfect vacation spot for kids and parents alike! From hands-on museums and lakefront adventures to deep-dish pizza and seasonal fun, this vibrant city has something for every member of the family. Ready to make unforgettable memories? Let’s explore all the reasons to vacation in Chicago with kids!
Things To Do With Toddlers in Chicago
Looking for fun, engaging, and toddler-approved activities in Chicago? Whether you're a local parent or just visiting with little ones in tow, the Windy City is full of exciting places to explore year-round. From hands-on museum exhibits and outdoor music classes to seasonal adventures across the city, this guide rounds up the best things to do with toddlers in Chicago—organized by season to make planning easy. Let the adventures begin!
Things To Do With Infants in Chicago
Exploring Chicago with a baby? The city has plenty to offer even its tiniest residents! Whether you're looking for calm, sensory-friendly experiences, stroller-friendly walks, or parent-and-baby classes that help you connect with your little one (and other parents), this guide rounds up the best things to do with infants in Chicago. From cozy indoor spots to peaceful outdoor outings, these activities are perfect for bonding, discovering, and enjoying the city together—one sweet moment at a time.
What to do in Chicago Every Season
Winter Things to do in Chicago
Think Chicago is only fun in the summer? Think again! ❄️ From twinkling lights and festive markets to cozy cafes and ice skating with skyline views, winter in the Windy City is full of unforgettable moments. Here’s your guide to the best things to do in Chicago when the temperatures drop—but the excitement doesn’t!
Fall Things To Do In Chicago
Fall in Chicago is a time to embrace the season's beauty, vibrant festivals, and cozy activities. From stunning autumn foliage to thrilling sports events and delicious seasonal treats, there's no shortage of things to do in the Windy City. Ready to make the most of fall? Check out our guide to the best activities in Chicago this season!
Spring Things to Do in Chicago
Looking for the best way to enjoy Chicago in the spring? From blooming gardens and outdoor festivals to iconic landmarks and hidden gems, discover the top activities that make the Windy City come alive in the warmer months. Ready to explore?
Summer Things to Do in Chicago
Coming soon.
Chicago Travel Itineraries
Chicago Girls Trip Itineraries
Looking to escape with your besties for a weekend of fun, food, and unforgettable memories? Chicago has everything you need to create the perfect girls' trip. From chic rooftop bars and trendy boutiques to cozy brunch spots and iconic sights, these handpicked itineraries offer something for every group. Whether you're here for a relaxing weekend or an adventure-packed escape, let me guide you through the best the city has to offer for a girls' getaway you won't forget!
Chicago Staycation Itineraries
Who says you need to travel far to enjoy a relaxing, adventure-filled vacation? Chicago offers a treasure trove of activities, hidden gems, and luxe experiences, all within city limits. Whether you're a foodie, art lover, or history buff, these staycation itineraries are designed to help you rediscover the magic of your own backyard. No passports required—just pack your weekend bag and get ready to experience Chicago like a tourist and a local all at once!
Romantic Date Ideas In Chicago
Looking to plan the perfect romantic date? It’s not about spending money or finding the flashiest location—it's about the thought, effort, and personal touches that make an experience unforgettable. In this post, I’ll share how forethought, time, and personalization turn any outing into something truly special. Whether you're celebrating a milestone or simply want to show you care, these tips will help you create a date that's as unique as your relationship. Ready to make your next date night unforgettable? Keep reading!
Food and Drink in Chicago
Best Restaurants in Chicago's Uptown
Craving a taste of Chicago’s hidden culinary gems? From vibrant Southeast Asian flavors on Argyle Street to cozy neighborhood spots serving unforgettable Puerto Rican dishes and classic chilaquiles, explore some of the city’s best off-the-beaten-path eateries that are sure to satisfy your food cravings!
Chicago Restaurant Guide
From mouthwatering deep-dish pizza to inventive fine dining and everything in between, Chicago is a food lover’s dream come true. In this guide, I’m serving up the best spots to eat around the city, whether you’re a longtime local or just passing through. Get ready to indulge in the diverse flavors, iconic bites, and hidden gems that make Chicago’s restaurant scene one of the most exciting in the country. Hungry yet?
