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Chicago Like a Local Blog

Unique perspectives on the city from the people who live here.

Author: Maddy Osman

Though early into her professional career, Maddy Osman is an eclectic "Jill" of the marketing trade. She's a wanderer at heart who accompanied her family as a youngin' to Nova Scotia, Canada and around the States, and more recently studied in Spain, visited China and will soon embark on a South American adventure. Between excursions near and far, she is happy to make Chicago her home, coming from a strong family tradition of Chicagophiles.  Check out her lifestyle blog ChicagoCheapAss.com for articles about living in Chicago on a budget.

Fall Date Night Ideas in Chicago

Tuesday, September 5, 2017 5:00 PM by Maddy Osman

Date Night can mean a lot of things to different people. From the usual eating out, be it at a fancy restaurant or your favorite neighborhood joint, to trying new experiences or even staying in, date night is a good way to bond with your partner, and keep the romance alive. Here are a few suggestions to keep your date night fresh and interesting in Chicago.

10 Free Things To Do in Chicago During September

Saturday, September 2, 2017 9:00 AM by Maddy Osman

September signals the end of summer and the start of fall. And although Chicagoans will miss beaches, music festivals and patio dining, there are still a lot of things to look forward to, like outdoor concerts, craft fairs, parades, and even free museum entry.

Here are the top ten cheap and free things to do in Chicago this September.

Shore Club: Chicago's New Beachfront Restaurant

Thursday, August 17, 2017 9:00 AM by Maddy Osman

Chicagoans have yet another thing to look forward to this summer, with the opening of Shore Club, an upscale development concept that brings the best of dining and hospitality to Old Town and Lincoln Park. The new multimillion-dollar beach-front bar, restaurant and resort is located at a prime Lakeshore Drive address (1603 N. Lakeshore Drive), and features floor-to-ceiling windows that offer the perfect sweeping views of Lake Michigan.

Chicago's Coolest New Concept Cafés

Monday, August 14, 2017 9:00 AM by Maddy Osman

Different concept cafés have been sprouting up left and right around the world, and represent a great way for business owners to infuse casual dining with fresh ideas. Some feature pop-culture characters and elements, while others are centered around objects or time periods, even being a spy, among other novelties. Many Chicago restaurants even choose to center their menu entirely to a particular kind of food (Ghirardelli Ice Cream & Chocolate Cafe, anyone?). Of course, Chicago, as a food-crazed city, isn't about to get left behind. Here are a few of Chicago’s new concept cafés we’re especially excited about, each with a sweet twist.

10 Free Things To Do in August

Thursday, August 3, 2017 1:00 PM by Maddy Osman

August means summer is soon coming to a close, so if you haven't been to the beach, or haven’t yet made it out to a music festival or free film screening, don’t sweat it. There are still plenty of fun warm weather activities lined up for the month of August, whether watching planes in the sky, or bingeing on the city’s signature sausage at food fairs and festivals around the city (one in particular this month). 

You’ve probably heard of Lollapalooza, an annual music festival featuring popular alternative rock, punk, heavy metal, hip hop and electronic music bands. The festival has provided a platform for non-profit and political groups, as well as both popular and underground visual and musical artists alike to showcase their work. The event itself started in 1991 and has counted France, Chile, Germany & Brazil amongst its list of host countries, though the Chicago festival is indisputably the best of these. Chicago has been hosting Lollapalooza since 2005, and attracts over 160,000 people during the now four-day affair.

This year, Lollapalooza takes place from August 3-6 at Grant Park, and features a star-studded lineup headed by Chicago’s own (and three-time Grammy winner) Chance the Rapper, American rock band The Killers, Muse, Arcade Fire, The XX, Lorde, Blink 182, and so many more. The full musical lineup and schedule can be viewed on Lollapalooza’s website or app.

If you haven't been to the Lakefront Trail in Chicago, you're missing a lot of natural beauty (all FREE for everyone to enjoy), efficient transportation to Chicago's neighborhoods, and a great opportunity to get in a workout. Here's why we love the Chicago Lakefront Trail, and some things you might not have known about it.

Freehand’s Chicago location is in the heart of River North, where you can find some of Chicago’s best restaurants, shops, and bustling nightlife. The funky boutique hotel is housed inside of a restored art deco building that dates back to 1927. Whether you’re traveling solo or with a group, Freehand has all of the amenities you desire.

More than being the center of Chicago’s entertainment scene in the 1920s and 30s, the Uptown neighborhod is known for its vibrant mix of history, culture and food. Featuring restaurants serving home-cooked recipes passed from immigrants that settled in Chicago generations ago, Uptown is a place every foodie should go for a taste of Asia and cuisines from the rest of the world. Here are 10 places we love in Uptown's dining scene, all serving unforgettable dishes under $10.

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