Chicago, North America Ana Rebeca Chicago, North America Ana Rebeca

How to Spend Your Time in Chicago During the Summer

There's nothing quite like summertime in Chicago. The Riverwalk, fireworks above the lake, rooftops and patios, and festivals galore! If you're planning a trip to the Windy City during the summer months, check out this travel guide on things to do in Chicago while you're visiting! You definitely don't want to miss out on this summer destination.

How to Spend Your Time in Chicago During the Summer: 10 Things to Do in Chicago

Now that summer is in full swing, travel season is too. Have you planned out which exciting city you're heading to next? New York, Paris, London, Los Angeles... All great cities. But they have nothing on CHICAGO in the summer.

Ask anyone who has been to or lives in Chicago during the summer and they'll tell you that all those cold winter months are worth living through solely because of the summer. Now I might be a littttlee biased, but I'm tell you--something about this city totally comes alive in the summer! It's like all of those months in hibernation puts us into action from late spring through early fall.

From rooftop bars to street festivals, the Riverwalk to Millennium Park, there are endless things to find, do, and eat here. If you're planning a trip to the Windy City during the summer, check out these tips on things to do in Chicago during your visit! Think of this as your "Chitown Summer Bucket List"!

 

1. Stroll down the Chicago Riverwalk

The city of Chicago recently invested a pretty penny into designing an amazing waterfront pedestrian walkway that is located on the south bank of the Chicago River. Visitors can come and enjoy a walk down by the river and stop in at the local wineries, restaurants, boat rental shops, bike rental stations, and more. You're right in the heart of downtown, which is wonderful to experience on a sunny day.

 

2. Head to Millennium Park for Free Activities

Millennium Park is sometimes scoffed off by locals as a tourist trap; but not in the summer! In the summer, Millennium Park has so much to offer visitors of all ages. There are free yoga and dance classes, free movies screenings, free concerts, free festivals, and more! What's better than free activities in the city?! For a full list of their activities from May through September, click right here

 

3. Visit Lincoln Park, the Zoo, and the Conservatory (all for free)

One of the city's best kept gems lies just north of the city center. The neighborhood of Lincoln Park is a must see when visiting Chicago (and it's where I call home!). Walk through the gorgeous park, visit the city's Lincoln Park Zoo, explore the Lincoln Park Conservatory, or relax by the Alfred Caldwell Lily Pool--all for free. It's a serene escape from the city without even having to leave the city. Try walking around the neighborhood if you have some time as well. It's very family friendly and full of boutiques, bars, and restaurants!

 

4. Shop the Farmer's Markets

There's something so nostalgic about a farmer's market in the summertime... Don't you agree? Chicago offers plenty of opportunities for farmers markets all around the city during the summer on various days of the week. You're guaranteed to get the extremely fresh food, beautiful flowers, and a lively atmosphere. There are even local restaurants that offer pop-ups at the markets from time to time! Check out the farmer's market schedule right here.

 

5. Attend a Festival

"Chicago" and "Festivals" are basically synonymous in the summer months. You can find a festival or event going on almost every single day in the summer--especially on the weekends. Attend fun events like Lollapalooza, Jazz Fest, Chicago Pride, West Fest, Taste of Chicago (or Randolph, River North, etc.), Art Fest, and even Hot Dog Fest. There are tons of different food, music, drink, or art related festivals going on throughout the summer, so make sure you don't miss out! Check out a full schedule here

 

6. Spend a Day On the River

If you're keen on spending the entire day by the water downtown, check out some of the other activities to do besides just the Riverwalk. You can go kayaking in the river, rent a boat or pontoon to cruise along the river, or you can take the uber-popular Chicago Architecture Tour. You basically get to spend the afternoon in a boat cruising around the downtown Chicago area while learning about the city around you. There are a few different companies that offer a Chicago River tour and, from what I hear, you really can't go wrong with any of them. Jay and I did one that was sponsored by the Chicago History Museum and it included a wonderful tour plus free drinks and snacks. I highly recommend it!

 

7. Drink at a Rooftop Bar and Eat on a Restaurant Patio

Ok, so I get that for those of you who live in warm climates you're probably thinking this one is silly; but in Chicago, rooftops and patios are a way of life in the summer. Like I said earlier, we're in hibernation mode during most of the year, so the minute it warms up--we are outside! 

Most restaurants and bars will start to open up their patio areas as soon as it hits decent temperatures (sometimes 50 degrees will do it), so take advantage of those when you can! See my list of places to eat in Chicago right here.

As for the best rooftops, check out some of these: J. Parker, Soho House, NoMI Garden, Cindy's, GreenRiver, Streeterville Social, or Rock Bottom. You can also browse the popular lists on Thrillist, Timeout, or Chicago Mag for more suggestions!

 

8. Spend the Day at the Beach

A lot of people look at me crazy when I say they should spend a day on the beach in Chicago, but it's a real thing that people do here! Thanks to Lake Michigan, Chicago's lakefront offers a nice stretch of "beachfront" property for visitors and locals to enjoy. You can party hard with the young crowd down by Oak Street Beach or North Avenue Beach (not my scene at all), or head a little further north towards Fullerton Beach or Montrose Beach to have a more quiet and relaxing experience. I personally love doing the latter with a little picnic in tow. Either way, I recommend you walk along the lakefront to take in the incredible views of the city and enjoy the lively atmosphere. 

 

9. See a Show

Chicago is an artistic hub for fascinating shows and brilliant performances. When visiting the city, you should definitely try to nab some tickets to see a Broadway play, a theatre performance, a dance performance, a comedy show, or a musical! The options are endless here and you shouldn't miss out.

My personal favorites are the dance performances put on by Giordano Dance Chicago, which is America's original jazz company. First of all, I love that the roots of jazz dance are here in Chicago and that this company has been thriving for over 50 years. Second, having grown up as a dancer myself, it's so inspiring to see the these incredibly talented professionals perform such moving pieces time and time again. I'm always so thrilled to see the new and innovative performances that their company comes up with! They typically have performances towards the beginning and end of summer (as well as throughout the rest of the year), and you can see their full schedule right here!

 

10. Explore the Neighborhoods

The Windy City is a neighborhood city, which means it's comprised of a ton of different areas and neighborhoods that all have their own unique personalities and vibes. The best part about being in Chicago when it's warm out is that you can actually enjoy the feeling of walking around and exploring the neighborhoods! Hop on a the L, take a bus, rent a bike, or get in a cab and head to a neighborhood that you want to see and explore it for a day. My personal favorites are Lincoln Park, Lakeview, Wicker Park, West Loop, and River North, but everyone has their preferences. You can check out more info on neighborhoods in my Chicago City Guide.

 

Also try:

  • Renting a Divvy bike and ride around town

  • Catching a baseball game with the Cubs or White Sox

  • Heading to Navy Pier to ride the new ferris wheel, or seeing the fireworks on Wednesdays and Saturdays

  • Exploring our world renowned museums, like the Art Institute or Shedd Aquarium

  • Renting a boat and venture out to Lake Michigan or tie-up to other boats in the "Play Pen"

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This list is just barely scratching the surface on all the incredible things there are to do here during the summer. Comment below with more activities that you love in Chicago!

 

Want more info on what to do during your visit to Chicago? Check out my complete FREE City Guide on Chicago. You'll find tips on airports, transportation, where to stay, when to visit, and much more!

 


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Chicago, North America Ana Rebeca Chicago, North America Ana Rebeca

A Foodie's Guide to Eating Around Chicago

If you need one reason to visit Chicago, do it for the food. Browse this guide of over 50 places to eat your way around Chicago's delicious food scene. 

A Foodie's Guide to Eating Around Chicago

If you need 1 reason to go to Chicago, go for the food. The Chicago food scene is absolutely booming right now. With rents skyrocketing in NYC and LA, chefs and restaurateurs are starting to see the value in bringing their businesses to the Windy City, which makes hungry Chicagoans very happy.

I've done my fair share of eating my way around the city the last few years and think it's time to pass along my knowledge to other foodies living in or traveling through Chicago. Whatever you're in the mood for, I've got you covered. I've included a place for almost every occasion you can think of--girls night out, cheap eats, power lunches, rom-din (new abbreviation for romantic dinner??), and even places #FTB. So without further ado, here are my top restaurant recommendations around Chicago! Bon appétit! 

 

Brunch

  • Summer House Santa Monica, $$, 1954 N Halsted St, *Retractable roof in the summer time!

  • Zella, $$, 1983 N Clybourn Ave, *Good spot if you want to party during brunch

  • Bongo Room, $$, 1470 N Milwaukee Ave, *Typically have seasonal menus, but red velvet pancakes are amazing

  • Taverna 750, $$, 750 W Cornelia Ave, *Great outdoor patio in the warm season

  • Blackwood BBQ, $, 305 W Lake St, *Amazing BBQ for any meal / More of a grab-&-go spot

  • Sable Kitchen & Bar, $$$, 505 N State St

  • Yolk, $$, 355 E Ohio St

  • La Creperie, $$, 2845 N Clark St, *Check out the darling patio in the back too!

  • Tavern On Rush, $$$, 1031 N Rush St, *Great location for people watching / Try the breakfast pizzas

  • Stanley's Kitchen & Tap, $$, 1970 N Lincoln Ave, *Near a ton of great sports & dive bars

 

"Power" Lunch

  • Slurping Turtle, $$, 116 W Hubbard St

  • Siam Rice, $$, 117 N Wells St, *Great power lunch spot to sit with fast service/ Basil Chicken is out of this world

  • LYFE Kitchen, $$, 413 N Clark St, *Very healthy spot with great food

  • Luke's Lobster, $$, 134 N LaSalle St, *One of the best lobster rolls in the city

  • HUB 51, $$, 51 W Hubbard St

  • Smoque BBQ, $, 3800 N Pulaski Rd, Ste 2

  • Bridge House Tavern, $$, 321 N Clark St, *Beautiful location along the river

  • Big Star, $$, 1531 N Damen, *Famous taco spot in Wicker Park / Cash only

  • Chicago French Market, $$, 131 N Clinton St, *Open market to walk through and stop at different kiosks

  • Bub City, $$, 435 N Clark St, *Cool, country vibe / Also has karaoke and live music on most nights

  • Protein Bar, Roti, or Freshii, $, Multiple Locations, *All great, fast eats for when you're in a hurry

 

Cheap Eats

 

Chicago Staples

  • Lou Malnati's, $$, Multiple Locations, *Best pizza in the city / The thin crust is delicious

  • Al's Beef, $, 169 W Ontario St, *Classic Italian beef sandwich

  • Portillo's, $, 100 W Ontario St, *Everything on the menu is amazing and you can't go wrong here

  • Pequod's, $, 2207 N Clybourn Ave, 2nd best pizza in the city IMO

  • Billy Goat Tavern, $, 430 N Michigan Ave, *Made famous by the likes of SNL

  • Wiener's Circle, $, 2622 N Clark St, *Go here late night for the "show"

  • Gibson's Bar & Steakhouse, $$$, 1028 N Rush St

 

Drinks & Sports Bars

 

Dinner

 

Sweets

 

This list is just scratching the surface on all the amazing eats there are in Chicago! Try these places out, ask other locals for their opinions, or walk around and stumble upon some quality spots yourself! You really can't go wrong with dining in Chicago...

What are your favorite places to eat in Chicago? Comment below with more spots!

PS - See my favorite travel things that I can't live without here!


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My Top 10 Favorite Speakeasies in Chicago

Sometimes I'm good at keeping secrets, but now I'm spilling my Top 10 Favorite Speakeasies in Chicago. 

My Top 10 Favorite Speakeasies in Chicago

I think one of the top questions I get in my inbox from readers (besides how I started becoming a blogger) is what are the best speakeasies in Chicago to visit when they are in town.  Chicago is, after all, known for being one of the best cities in the world for speakeasies thanks to our man Al Capone and the Prohibition Era.

Well...I decided to compile a list for all of you since I keep copy-and-pasting the same ones over and over in my emails.  Here is a list of my Top 10 Favorite Speakeasies in Chicago.  Bottoms Up!

1.     Violet Hour

Wicker Park, 1520 N Damen Ave.

Violet Hour: my absolute favorite spot in the city for a drink.  Chances are you have walked by this famous Wicker Park institution and not even known it.  The main door is always camouflaged behind a massive, ever-changing mural that is painted across the building’s wall. 

Step inside this place and feel like you are being transported to an Alice in Wonderland-esque world.  The cocktails are to die for, and they have a no cell phone rule—so put them away!

2.     The Drifter

River North, 676 N Orleans St.

Located in the basement of The Green Door Tavern you will find this vintage-looking REAL speakeasy from back in the day.  Just walk downstairs like you are going to the bathroom and knock on the bookcase (that is actually the door) that is on your right.

The drinks are presented on tarot cards for you to order from, and they have live music and burlesque shows through the week.  *Check out the old door hanging on the wall inside because that is the original door from the Prohibition days!!

3.     Door No. 3

Wicker Park, 1572 N Milwaukee Ave.

So I kind of have a soft (and angry) spot for this place because I got my fake I.D. taken away at the Double Door when I was underage... BUT—all is not lost because Door No. 3 is Double Door’s speakeasy basement lounge and it is really fun.

You’ll find the entrance in the alley off of Damen and under the Blue Line tracks.  You’ll find DJs spinning and drinks flowing down here.

4.     Untitled

River North, 111 W Kinzie St.

Untitled is like the mega-venue of speakeasies in Chicago.  You will probably miss the entrance unless it is a busy night of the week when there is a line outside the door.  Despite the line, it is definitely a place to check out.

There are 3 massive rooms when you walk downstairs, and each of them has a totally different vibe.  Sit in the dining hall (with private booths) for some dinner.  Enter the library for a cocktail, to catch an old black and white movie, or to gaze at the giant wall of private lockers that holds the members' booze. Last, you can head to the back room for live music and entertainment.

5.     Double A

River North, 108 W Kinzie St.

Just across the street from Untitled is another great spot in the basement of Mercadito.  Down there you will find the cute, tiny speakeasy Double A.  Drinks are delicious and space is limited, but it is always a great time.

6.     The Green Mill

Uptown, 4802 N Broadway St.

Another Prohibition-original, this place used to be a popular hangout for the (in)famous mobster Al Capone and other celebs of the day.  Capone’s favorite booth is still in the lounge located directly west of the short end of the bar.

Nowadays, you can catch amazing jazz music and other live performances while sipping your cocktails.

7.     Barrelhouse Flat

Lincoln Park, 2624 N Lincoln Ave.

When you walk into this place, you wouldn’t think there was any type of speakeasy vibe to it at all.  All you have to do is just head to the back of the bar, go up the stairs and there you go!

The upstairs bar here is a great spot to have a more quiet experience than you will have downstairs, and you’ll be served much better cocktails.  The decor is to die for!

8.     Bordel

West Town/Wicker Park, 1721 W Division St.

Going back to my Latin roots, Bordel gives me everything I need in a speakeasy.  Open the door to the right of Black Bull (which is one of the best tapas restaurants in town), take the stairs up, and the unmarked door will be on the left.

You can expect amazing cocktails and live performances from music to burlesque.  My personal favorite:  Flamenco Dancing on Saturday! Ahhh... it’s wonderful.

9.     Three Dots and a Dash

River North, 435 N Clark St.

Chicago gets pretty damn cold most of the year, so us locals need a tropical escape from time to time.  Thankfully, there is Three Dots and a Dash to tickle that fancy.

This tiki inspired speakeasy is located in the alley behind Bub City.  Once inside, follow the massive wall of skulls down the stairs to enter the tropical drinking hole. You’ll find a massive drink list that resembles something you would get at a hotel resort on the beach. You and your friends could even order a giant treasure chest filled with dry ice and Dom Perignon to share at your table!

10. The Office

West Loop, 955 W Fulton Market

This spot is definitely the trickiest of all speakeasies on this list to get into.  It is located in the basement of The Aviary (which is an unbelievably amazing cocktail lounge that you must go to as well) and you basically need an invitation to get inside.

You can try to politely ask around upstairs for an invitation, or book a private party for up to 16 people and you are almost guaranteed to get in.  The cocktails here and upstairs at The Aviary are among the best in all of Chicago.

 

What are your favorite speakeasies? Comment below with more great locations!


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Chicago, North America Ana Rebeca Chicago, North America Ana Rebeca

Indoor Skydiving in Chicago

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Indoor Skydiving with iFLY

A few days ago, my mom told me that she had a brunch surprise planned for me on a Friday at 9am. Not being a morning person, I rolled my eyes at the idea of having a wake up so early to go somewhere for “brunch” at that hour. My mind was blown when we drove up to what she actually had in store...

She had signed us up for an indoor skydiving session at iFLY Chicago, which is located just out of the city in Rosemont. I instantly thought, “Wow...I officially have the coolest mom ever!!”

Indoor Skydiving

Our indoor skydiving session started out with a quick training video and training session from our instructor. They show you the proper way to get in and out of the wind tunnel, the proper way to move your body around, and answer any other questions the students have. I went in knowing absolutely nothing and left being a total expert.

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After the instructions, it was time to suit up and get in the tunnel. They provide you with your suit, goggles, helmet, and earplugs. A typical admission will get you about three 1-minute turns up in the wind tunnel with the instructor. However, you can pay a little extra and get 2-minute turns, which is what my mom and I did. It was so much more worth it to do the longer turns.

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The experience was so exhilarating and fun. They even have a camera that takes pictures and videos of you while you are flying! I’ve never been skydiving (too afraid of heights), but indoor skydiving was just perfect for me. It was a great “brunch” treat from my mom to start off the weekend.

Click HERE to find an iFLY near you!


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Chicago, North America Ana Rebeca Chicago, North America Ana Rebeca

Cake Decorating in Chicago

Cake Decorating with Give Me Some Sugar

Looking for a sweet treat in the city or something fun to do on the weekend? Look no further than Roscoe Village’s Give Me Some Sugar’s Cake Decorating Classes. This adorable cake studio is available for all skill levels and offers cake decorating, cake ball/pops classes, fondant classes, cookie decorating classes, and so much more!

My mother has just about everything that a woman can ask for, so I started gifting her “events” and things for us to do as holiday presents. Instead of the typical socks or cookbook gift that I could get her, I started giving her vouchers for fun activities for us to do together.

Cake Decorating

We stopped in at Give Me Some Sugar a few weeks ago to try out their intro to cake decorating class. It was a fun class that lasted about 2.5 hours with all materials included.

cake decorating class

Give Me Some Sugar is so beautifully decorated inside (I felt a cute modern-day Marie Antoinette vibe with all the decor in there) and a fun stop for people looking for a unique activity to do through the week.

During the Cake Decorating class, we learned how to properly make the cake, create designs, and use the different colors that were supplied. The instructors are there to help through the entire process and to answer any questions you have.

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The ladies at Give Me Some Sugar give you all your supplies and walk you through the entire process of what you need to do for your class! Everything that you make, you get to take home with you. My mom and I are even gluten-free eaters and found out that you can order gluten-free products if you call ahead of time--which I definitely will be doing when I go back! Just wear clothes you don’t mind getting dirty and standing in for a while.

Cake Decorating

Click HERE to see cake decorating classes from Give Me Some Sugar


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Chicago, North America Ana Rebeca Chicago, North America Ana Rebeca

Flying Trapeze School in Chicago

Trapeze School in Chicago

This year I’ve been attempting to get out of my comfort zone with everything I do and expand my horizons. Think a la “Yes Man” where I try to say, “Yes” to things that I probably wouldn’t normally do. One of my adventurous girlfriends asked me if I wanted to do a flying trapeze class with her here in Chicago. Keeping true to my new mantra, I said, “YES!” We signed up for a class through the Trapeze School NY Chicago, which you can check out HERE.

Trapeze School Chicago

As someone who is a little nervous with heights, it was such an exhilarating feeling to try this new flying trapeze activity. I was put at ease by the fact that you are totally strapped in with a net beneath you and there are trained professionals all around.

The first jump, I totally freaked out and screamed the entire way. The sensation was so crazy and unnatural! But after a few tries, I got the hang of it. The instructors were so amazing and really helpful. They gave everyone step-by-step instructions for what to do at what time. You're totally safe and in good hands with them.

Trapeze School in Chicago
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The class lasted about 2 hours and we each got to go at least 5 times on the trapeze. Definitely wear comfortable clothing, longer pants (I wore yoga pants), and socks that cover your ankles and heels (some of the tricks can hurt if you don’t have this!).

It is such a fun activity to do in the city! In the summer, they even take the class outside and you get to do the tricks out in the fresh air. I'll definitely be going back again soon! See local classes and times for the trapeze school in Chicago HERE.


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Chicago Ana Rebeca Chicago Ana Rebeca

Soho House Chicago

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Soho House staycation and relaxing hard this weekend - Chicago, Illinois

This last weekend I stayed at the Soho House Chicago for a nice (and much needed) staycation after the hectic holiday season.  The Soho House is known for having high quality service to their members and guests alike, so I was very excited to try out their accommodations as a hotel guest this time.

First of all, I blame the bed and pillows for the reason why I barely moved all weekend.  The combination of all the huge, fluffy pillows and that unbelievably comfortable mattress was a recipe for greatness.  I would recommend staying at the Soho House solely just to experience this.  The rest of the amenities provided in the room were wonderful as well.  They even provide a lovely tea set that you can utilize in your room during your stay.  A notable mention also goes out to the amazing rainforest shower that is in the bathroom, which came fully stocked with every Cowshed product possible.  Smelling all of those delicious scents of shampoos, conditioners, body wash, and body scrubs made me want to run downstairs to the spa and buy every last bottle!  It was such a nice touch and much better than having to use the tiny hotel sized products that you normally get while traveling.

The Soho House definitely did not disappoint me during my stay as a hotel guest there.  It was as relaxing, lovely, and elegant as I hoped it to be.  I would gladly return to do a staycation there again!  Click HERE to check out Soho House Chicago.

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Hi, I'm Ana Rebeca! Welcome to The City Sidewalks. Here you’ll find tips on Travel, Lifestyle, and Wellness.

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