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three-day long weekend itinerary for Chicago

Posted in Travel by

Chicago is the greatest place in the world, and I’m not the only person who thinks so!

There’s something to do 24 hours a day here, which makes it the perfect city for a three-day weekend vacation. You’ll get a lot of bang for your buck with its easy accessibility (two airports, an Amtrak and Greyhound station, and plenty of city-wide public transportation to get you where you want to go), things to do in any weather or season, and relatively central location.

Day One

Spending your first evening downtown is great, because you can knock out a lot of city “must do”‘s in one location. Grant Park, Chicago’s front lawn, is home to the Bean, Buckingham Fountain, and many other public artworks. Take a selfie at the cloud, grab a Divvy bike and admire Lake Michigan from the Lakefront Trail, and in the winter months, skate on the ice rink!

Rainy day? Stay dry and see the city anyway on one of the many bus tours! From crime and mobster history to architecture and Chicago lore, there’s no lack of ways to

For dinner, start your Chicago food tour off right at Pequod’s Pizza, which I think is the best deep dish in the city! They also have thin crust and many non-pizza options as well.

Afterward, hop on a Divvy Bike to burn off some of that carb-y energy and head over to the Riverwalk, where you can take your pick of a post-dinner treat while walking the trail. It’s also near the Magnificent Mile so you can scratch that shopping itch at souvenir shops, Water Tower Place, or other major retailers like Apple, Louis Vuitton, and more. (Like a Nutella Cafe. You’re welcome.)

Day Two

On Saturday morning, grab a coffee from Fairgrounds or Goddess and the Baker and stop by the free Chicago Cultural Center. With rotating exhibits and stunning architecture, it’s a popular spot for new visitors and locals alike.

Then, head over to Old Town and grab a table at The Whale or Farmhouse, depending on your party’s tastes. Stick around the neighborhood to hit another one of the city’s most “can’t miss” institutions, the Lincoln Park Zoo! They’re open 365 days a year and is always free of charge. (Concessions are surprisingly affordable, too.) Visit Alexander Camelton, check out some presentations by zookeepers and volunteers (I especially love learning about the polar bears and sea lions) and walk around another one of the city’s amazing parks. If your zoo day is rained out, the Chicago History Museum sits at the south end of the park.

Hop on the Blue Line to the Damen stop to spend the rest of the afternoon in trendy Wicker Park and Bucktown. Grab a tasty treat from Stan’s Donuts, stop in to bookstores VolumesMyopic, and Quimby’s (all independent, all great for their own reasons,) and pop into Corbett vs. Dempsey, a free art and culture museum in the Dusty Groove building. Wicker Park is also a great spot to grab an Italian Beef, a classic meal – Jay’s Beef is easy to get to.

Rainy day? Try out an escape room – we have them all over the city. If you don’t like solving puzzles, try a more traditional arcade, like Headquarters Beercade or Emporium. My favorite is Ignite, a video game lounge in Skokie and Avondale – I could play Rock Band for hours and hours (and have on more than one occasion!)

For dinner, since you’re already in Wicker Park, make a beeline for Small Cheval. The little sister restaurant of Au Cheval, it’s more affordable and more relaxed, but still serves one of the city’s best burgers. Their shakes and fries aren’t anything to shake a stick at, either!

The Second City has been home to more successful comedians than you can count. They have several stages and several shows every night, so do yourself a favor and stop by to see the next big things.

Afterward, hop over to Humboldt Park and my favorite bar in the city for a nightcap – The California Clipper is a dimly lit former 1930’s movie theater with a speakeasy feel. Opening at 8, it can often be empty for the first few hours, which always makes me feel like I have some kind of secret gem in the city. That doesn’t last long, though – once the music starts and 10pm approaches, you’re lucky to grab a spot to stand, and the party keeps going until 3am. Grab a Pago Pago with old-fashioned shaved ice… so good.

Day Three

Spend a low-key Sunday morning in the Andersonville neighborhood. Foursided, Woolly Mammoth, and Women and Children First are just a few of the funky specialty shops you’ll find here. When your feet are tired, your arm is weighed down by reusable shopping bags (Chicago has a bag tax, which will add up after a long weekend!), and your wallet is feeling light, grab one of the best brunches of your life at Big Jones.

On your way out of town, head south to Pilsen. This up-and-coming neighborhood is growing fast – in the span of a year there have been so many new businesses, restaurants, and events popping up that there’s always something new to do!

Grab dinner at the award-winning Dusek’s in the historic Thalia Hall building, or head downstairs to one of my favorite spots in the city, Punch House. With a cool 70’s vibe, boozy punch on tap, low lighting, board games and cozy booths, it’s a great spot to unwind and end your time in the city!

None of these activities sound like your speed? Don’t worry – the city of Chicago’s got your back. Request a Chicago Greeter to show you around and get a personalized offbeat experience!

August 30, 2019
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january 2019 book club

Posted in Entertainment by

book club book reviews

New year, new books, new me! Or something like that. I read A LOT in January, which I attribute to getting a library card for my new city, which has the most amazing library. I also started listening to more audiobooks again – often while playing a video game, because my boyfriend got me hopelessly hooked on Mass Effect – and I also picked up several graphic novels, which are usually quick reads.

I still love my Kindle – especially the feature that lets you check out library books – and Amazon’s Kindle First Reads have been really great lately too. (They offer six free books to choose from every month, so you can read them before release.)

Let’s dive in!

The Great Believers: Wow. Wow wow wow. This is the most incredible book I’ve read in a long time. It’s set in 1980’s Chicago – during the AIDS pandemic – and present(ish) day Paris. I wondered how the two storylines would intersect, and if it would make sense, but it does – and wonderfully so. To avoid spoilers, it’s hard for me to describe the book any more specifically than that, but I felt deeply for the characters, invested in their wellbeing and happiness. We went to visit friends while I was reading this, and they live in the neighborhood much of the novel takes place in, and I was just excitedly looking around at the places mentioned in the book. (I realize not everyone can have that experience, but it’s fun when a book can make you excited about your city.) Don’t hesitate, just pick this book up and read it – you won’t regret it.

Taking Turns: Following my binge of The Great Believers, I was reminded of this graphic novel that’s long languished on my TBR list. Written by a nurse who worked on Chicago’s only dedicated AIDS ward (a place many characters in the book spent time), it’s a really affecting account of the disease’s impact on families, the staff, and the city. It’s a great follow up to The Great Believers.

Like reading on your computer or mobile device? Check out Scribd – thousands of eBooks, audiobooks, magazines and more on your device!

My Year of Rest and Relaxation: This book had a lot of hype around it, and rightfully so. It’s not often that I hate a narrator but still enjoy the book, but that’s the point – rather than facing her problems, she finds a psychiatrist and uses her to basically sleep through a full year. Set in 2000, it’s an interesting time period, when it was maybe a little easier to slip through social nets and avoid and ignore people. Though I hated the character, the writing and story was amazing. This is a good one to curl up with on a subzero weekend.

Kitchen Confidential: Despite my love of the Food Network, I’ve never watched an Anthony Bourdain show. I still haven’t, but I loved listening to this audiobook. It’s fascinating, and I liked how he didn’t pull any punches about addiction in the restaurant industry, or the crazy hours and crazy hours, resulting often in crazy lives. It’s a really great food memoir, and it’s a heavy recommend from me.

Speak: The original novelization of this book was a favorite of mine in high school. I loved the mystery – what happened? Why did she refer to this guy as “Beast”? – and was very excited when I learned a graphic novel had been published last year. Unsurprisingly, I read this book in one sitting the night I brought it home from the library. The illustrations capture the story well, and the revelation scenes are really well done. Graphic novels aren’t all comics and jokes, and Speak is an excellent example of that.

The Four Tendencies: When we picked the “book about personality types” prompt for the reading challenge, I knew immediately I was going to read this book. Gretchen’s podcast is great, so I listened to the audiobook while working, and it had a lot of interesting insights. While it’s always fun to hear about your own personality type, there were a lot of suggestions on how to interact with other personality types, including kids. I made Evan take the quiz to see what his result would be, and it was exactly what I had expected. He asked what my type is, and I said “what do you think?” I can’t imagine a more perfect response from a Questioner.

Sick: I ABSOLUTELY LOVED THIS BOOK. America’s health system is broken, for sure, and this is the story of a writer who struggles with getting care and a diagnosis often without health insurance, a consistent primary provider, and the stigma of being brown, a woman, and having a history of addiction. After many years (and many caretakers, a marker of her illness), she gets a diagnosis and learns the early signs of a relapse. As someone who has been through rounds and rounds and rounds of medical testing, often without resolution, this book felt very familiar and truthful.

Wondering how I read so much? My libraries use Libby – see if your library has a partnership, and check out the mobile app!

Fun Home: This graphic novel about a woman’s relationship with her father and the lies she uncovers as she grows up and comes out is really beautifully done. The artwork is lovely and I liked the way the story started to finally weave together in the end. I didn’t love it as much as some other people do, but I didn’t dislike it by any means, and it was a nice read.

Lush: Unsurprisingly, my obsession with addiction memoir continues. I haven’t read any of Kerry Cohen’s previous work, but she makes several references to topics covered in her first two memoirs, and they sound great. I related to a lot of this book – I’m getting to the sort of awkward age where a lot of things center around drinking, and I’m tending more toward red wine. Not that I needed any cautionary tale, but this is a great look at problem drinking outside the stereotypical 20’s college student.

What did you kick off the year reading?

February 1, 2019
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2018 gift guide: Chicago lover

Posted in Shopping, Travel by

2018 gift guide chicago gift ideas

It’s that time of year again! Holidays always seem to be the time of year where we feel totally stumped by the people we want to gift. Either they have everything, or they don’t “need” anything. Sometimes it’s a really nice gesture to take a deep look at the recipient’s personality and connect that to any gifts you want to give them. It’s a good tip to keep in mind year-round!

For travel lovers, it might be nice to help them pay homage to their favorite place. Since I love Chicago, that’s the theme of today, but many of these gifts are available for other cities and states as well. Let’s take a look!

Chicago Bears travel scarf: I have one of these Waypoint Goods travel scarves and I absolutely love it. I hear the Bears aren’t really something to be proud of, but there are plenty of other colors to choose from too! This cozy infinity scarf features a pocket big enough for your phone, cash, and earbuds. Carrying a purse has become such a burden, so I’ve pared down my everyday carry items to fit in this pocket, and I love it.

Chicago Skyline print: Local printers and artists at Foursided have my heart. This skyline print is my favorite, but there are tons of other options if you prefer a map motif, something more mid-century inspired, or want to pay tribute to the long-suffering Cubs.

CTA Stop Magnets: If you’re like me and live in everyday thankfulness for the vast CTA system, Transit Tees has the gifts for you! Tell your friends what line or stop is your favorite – Transit Tees makes magnets and pins for almost all of them. I got the boyfriend a Yellow line magnet as a housewarming present for the new house, so this is a great shop to keep in mind year-round!

Chicago Homesick Candle: Homesick Candles have been around for awhile, but I still totally love them. The Chicago scent hearkens Fannie May chocolates and the breezes from Lake Michigan. The Illinois version of the candle carries more floral scents.

Chicago Flashback: This book from the Tribune staff would be a great gift for a history buff. It not only showcases photos of our beautiful architecture, but also tells the stories of the builders and other notable Chicago residents.

Chicago Skyline Lego Set: Somehow, the older I get, the more I regress into enjoying Legos. I’ve always been freeform and abstract with mine, but this Chicago skyline set is really cool. My grandpa worked on the Sears Tower when it was being built, so it would be a fun homage to that. (And no, I will never call it the Willis Tower.)

Chicago-opoly: This fun Chicago-themed Monopoly-style board game would be a hit for me. I love attending and hosting game nights, and Monopoly is best suited for a long weekend because as everyone knows, it’s a marathon game! This is a great gift idea for someone you don’t know well, because the odds of them not liking fun is… well, pretty low.

Chicago-etched Whiskey Glass: I love these types of whiskey glasses. They’re well-made and the etched Chicago map makes it feel a little fancy.

How is holiday shopping for you? Do you find it difficult, or are you like me, finishing before Thanksgiving even hits?

November 19, 2018
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doing Chicago: 24 hours of fitness

Posted in Travel, Work Out by

fitness in chicago

Chicago is a city that’s screaming to be explored by foot power – with tons of different gyms and unique classes to check out. There’s nothing I love more than taking a walk around any of our neighborhoods – there’s always a ton to see, and you’ll almost certainly stumble into a fun street festival or farmer’s market in the summer. It’s one of the most fit-friendly places in America, so if you’re looking to see the city while you get fit, here’s a 24-hour guide to Chicago fitness to follow!

9:00 AM: Head out of your room at the Chicago Athletic Association for a run through Grant Park and along the lakeshore. The hotel was built in the 1800’s as a club for society men to shoot pool and work out, and it’s still decorated with a sporty spirit today. Head north on Lake Shore Drive past Buckingham Fountain, Cloud Gate (more commonly known as “the Bean”,) and follow the path up to Oak Street Beach. Part of the Rock ‘n Roll 10K I ran last summer went along the lakeshore and ended in the park, and it’s really beautiful and inspiring if you depend on scenery to distract yourself from running. Take some time to relax on the beach and cool off, then head out to refuel.

Photo by Sawyer Bengtson on Unsplash

Cloud Gate at Millennium Park

11:00 AM: Try Wicker Park for brunch – whether you’re looking for something healthy (try Native Foods Cafe) or sinful (Stan’s Donuts is a must-try,) there’s something to satisfy everyone in your group. Afterward, take a walk over to Cup & Spoon (2415 W North Ave.) to grab a glass of their Electric Lemonade – the activated charcoal in it will help out with any tummy trouble building up.

From there, it’s a short walk to the Divvy station at Western & Winnebago. Divvy bikes let you rent for a few hours or a whole day, so check one out and take a spin on the 606 trail. A former el line, it was recently renovated into a gorgeous 2.7-mile trail that’s bike- and run-friendly. Markers line the trail with Chicago history and landmarks, so you can learn as you lean!

1:00 PM: Head back downtown on your bike and grab another quick bite to keep your energy levels up. I’m a really big fan of Sweetgreen (huge, fresh salads) and The Protein Bar for great juices and wraps.

2:00 PM: Continue your tour of Chicago architecture and history with a tour on the river. Kayak Chicago offers several different tours, including an architecture tour, so you can appreciate the gorgeous 1800’s buildings in downtown (and scout out those riverwalk bars to visit before heading home for the night.)

5:00 PM: Green Zebra is the perfect dinner for your fit day. A vegetarian restaurant specializing in small plates, their menu is creative and changes seasonally. The tasting menu is a nice way to make the meal special!

7:00 PM: Finish up your day of fitness with a fun dance class. Stiletto Dance Studio offers classes in bootcamp and yoga, but if it’s a girls trip: head there for the Pole Dancing classes and get your groove on. (Or if you’re still feeling up to it, try stand-up-paddle in Lake Michigan with Chicago SUP. It’s beautiful at night.) In the summer, there are often dance parties in city parks, like salsa, mambo, and bachata classes

Photo by Ardian Lumi on Unsplash

9:00 PM: Head to Logan Square and hit up the local barcade, Emporium. You and your friends can keep up your competitive spirit with games like air hockey or pool, or stick to the solo machines like Pac-Man and pinball. (Try a local Chicago brew, like Revolution, while you’re there – beer is a great way to replenish nutrients your body loses after a hard workout!)

8:00 AM: Since you went to bed so early, you’re surely waking up and feeling great! Before heading out of town, grab some Dark Matter coffee and check out Flywheel. It’s similar to Soulcycle (but more accessible to newbies,) and they often have Chicago-centric classes. If you aren’t going to Pitchfork festival, you could at least go to the Pitchfork Flywheel class! Afterward, head to Lincoln Park’s Chicago Pizza and Oven Grinder Factory. You deserve it after all that work, and it’s a Chicago institution!

What’s your favorite way to actively explore when traveling? Do you have a favorite Chicago workout spot?

June 1, 2018
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doing Chicago: cheap and free music festivals

Posted in Travel by

free festivals in chicago

Chicago in the summer is the best place in the world. (I haven’t been everywhere, but I’ve been enough places to be pretty convinced.) One of the best things is our seemingly unlimited supply of free street festivals – there’s something going on every weekend, and even during the week. Music festivals are super popular and run all summer, from Do Division the first weekend in June through the end of October, so check out these cheap and free Chicago music festivals!

Bookmark this post and come back all summer to find activities to check out!

Weekly Events

Navy Pier Beer Garden: The Miller Lite Beer Garden at the end of the Pier features performances almost every day of the week. Beer here is also super reasonably priced, and the gorgeous views of the city as the sun sets is totally worth the schlep out to the shore from whatever neighborhood you’re in. Check out their calendar for music events, plus other great free things to do while you’re in Chicago.

Haymarket Brewery: On Thursdays, Haymarket Brewery has an Americana music series featuring a lot of my faves and friends from Nashville. This is actually a year-round series happening every week, so pop over for some great brews and tunes, even in the dead of winter!

Grant Park Music Festival: Grant Park is home to the largest outdoor classical music festival, which is pretty cool. Events here feature the option to purchase tickets, otherwise, GA seating is always free on the back of the great lawn. Special guest conductors and performers and performances of classical greats is an excellent way to add some culture to your Chicago trip, without adding a big price tag.

Annual Events

June

do division

Photo via Do Division Facebook

Do Division Fest: Do Division is sort of the symbolic start of summer for me. It’s the first weekend after Memorial Day on one of the coolest stretches of West Town. This year’s headliners include Ted Leo and the Pharmacists, Deerhoof, and Bear Vs. Shark – not bad for a free street fest! In addition to eight(ish) hours of music at two stages per day, there’s also a sidewalk sale with local artists and vendors, a family fun festival with activities for the kiddos, the shops on Division set up their sales outside, and restaurants expand their patio seating.

Andersonville Midsommarfest: Andersonville on the north side is a really fun and diverse area, and from June 8-10, they present a great street festival. A $10 donation goes to the neighborhood chamber, and you can take part in yoga, check out music, shop the vendors and sidewalk sales, and eat until you can’t eat anymore. Andersonville has a heavily Swedish heritage, so partake in some traditions like dancing around the Maypole and eating Swedish food (it’s more than just meatballs.)

Chicago Blues Festival: This free festival in Millennium Park is also June 8-10, so if you’d like to stay closer to downtown, stop in for a set here. I love picnicking at Millennium Park, and there’s a Mariano’s nearby – pick up some snacks and a bottle of wine for a cheap, romantic date downtown. The incomparable Mavis Staples caps this year’s festival on Sunday night at the Pritzker!

Taste of Randolph: Three stages in the West Loop along Restaurant Row? Sign me up, please! This festival is pretty long-running, and this year will take over Randolph Street from June 15-17. The lineup is insane – I can’t wait to see Mayer Hawthorne and the amazing MONAKR again – for a $10 entry donation. Taste of Randolph is definitely a can’t-miss event for your weekend in Chicago!

Logan Square Arts Festival: This is a small music, arts, and family festival in Logan Square. One of my favorite bands, Priests, is playing this year, and I’m excited to pick up some enamel pins from local seller Jini & Tonic!

July

craig finn at west fest

West Fest: Another festival that shuts down along a stretch of great restaurant options, West Fest is July 6-7 this year. The first time I met Craig Finn was at this festival, so it holds a dear place in my heart. It’s on the smaller scale, so if you get overwhelmed by the big crowds at Grant Park or Taste of Randolph, this is a great one to head over to. A small kids area is far away from the stage to protect their hearing, food trucks park at the end of the street, and vendors line the road. (My suggestion? Grab dinner at Roots Pizza. Soooo good.)

dessa at square roots festival

Dessa at Square Roots Festival 2016

Square Roots Festival: This festival in Lincoln Square gets some pretty heavy hitters every year – the first year I went, it was my first solo Dessa show, and I was just delighted. (I heard her sound check start, thought I was running late to the show, and ran in on crutches… only to realize it hadn’t yet started.) This year Square Roots is from July 13-15, featuring Nashville favorite Pokey LaFarge and Chicago locals Get Up With the Get Downs among (many) others. A $10 donation gets you through the gates for the full weekend (and benefits the Old Town School of Folk Music), and like many other festivals, there are lots of vendors and family-friendly activities. I remember this festival as one of the best food spots – it felt like the food and beer options went on for miles!

doomtree at wicker park fest

Wicker Park Fest: Wicker Park/Bucktown is still my favorite part of Chicago, and Wicker Park Fest is July 29 and 30 this year. It’s a $10 suggested donation for admission, but they shut down part of Milwaukee Ave., put up three stages for music, and fill the street with vendors and Goose Island beer. There’s also a kids festival here. Headliners should be announced in a few weeks, and after Doomtree and Guided By Voices last summer, I’m not sure how they can top it this year!

August

Big Evanston Block Party: I’m really excited for this first-year block party. SPACE in Evanston is one of my favorite venues here, and from August 25-26, they’re celebrating ten years of concerts. Two of my favorites are headliing – The Old 97’s and Guided by Voices – so I can’t wait! It’s a free festival with options to purchase VIP upgrades, but it looks like early registration is required, so grab your August 25 and August 26 tickets early.

September

Chicago Jazz Festival: This festival is where I lost my keys last year, but I’ll try not to hold that against them. Sitting on the lawn here, sipping bottles of wine picked up at Mariano’s nearby, and watching the sun set over the city skyline is such a nice, relaxing way to say goodbye to summer.

goose island 312 block party

312 Block Party: This Goose Island party represents the end of summer to me. 2018 dates haven’t been posted yet, but it’s typically the third weekend in September. Last year, Ted Leo and the Pharmacists headlined, and in 2016, Beach Slang was my favorite set. Word on the street is that this year, the Empty Bottle is bringing in the best lineup yet, and another bonus (besides the beers and excellent brews?) Grab Hot Doug’s from the food area here, which is a Chicago classic.

Did I miss any other free Chicago music festivals? Let me know what your can’t-miss picks are!

May 23, 2018
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