How to Spend 72 hours in Lakeview East and Wrigleyville


Welcome to Chicago! Home of deep dish pizza, Chicago-style hot dogs, and skyscrapers as far as the eye can see. Spending time in Lakeview East will cross off dozens of items on your “Must Do In Chicago” checklist. Home to Wrigleyville and the very popular Boystown, Chicago’s inclusive LGBTQ+ neighborhood, there is something for everyone here in Lakeview East. Here’s how to spend 72 hours in LVE!

1. Visit Wrigley Field

Visit the oldest ballpark in the National League and cheer on our Chicago Cubbies! Wrigley Field is a beautiful historic ballpark you must see during your stay. Go for a Cubs game, or take a photo in front of the insta-worthy marquee. Inside the ballpark, you’ll see Cubs memorabilia, Chicago-style hot dogs, and enthusiastic fans decked out in red, white, and Cubby blue. Directly outside the ballpark, you’ll see Gallagher Way, a park that hosts open-air activities year-round. Watch a free movie on their massive projector, visit their French Market, or see an outdoor concert! There is always something good happening at Gallagher Way, click here to see the full schedule.

Pro Tip: We recommend checking out Murphy’s Bleachers to see TONS of Cubs memorabilia and to really feel like a local! Murphy’s is directly behind Wrigley Field.

2. Eat Like a Local

Us Chicagoans take pride in knowing we have some of the best food in the country. Famous for three things in particular: Chicago-style hot dogs, deep dish pizza, and roasted Italian beef. Check out our Dining Guide (LINK) to know where to go for top notch Chicago cuisine.

Hot Dogs: A Chicago hot dog is a beef hot dog on a poppy seed bun, decorated with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato, pickled sport peppers, and a dash of celery salt. Notice how ketchup is NOT listed as an ingredient, and any hot dog stand owner will tease you if you ask for it (however most places will provide you with it). Clark St Dog is an ideal place for you to get your first Chicago dog. This fast food joint has been serving since 1977 and they never miss. We recommend grabbing a pickle back shot while you are there since they are the home of the pickleback! Open till 1 am Sunday-Thursday and until 2 am Friday and Saturday, enjoy your dog at any time.

Spending a majority of time in Wrigleyville? Check out Wrigleyville Dogs located right on Clark Street! Family-owned and operated since 1991, grab a dog and enjoy it inside or on their patio. You can grab a Chicago style dog, french fries, and a soda for just $7.30! Do yourselves a favor and grab an order of mozzarella sticks while you are there. If you find yourself on Broadway street, a bustling street filled with local shopping and entertainment, grab your hot dog from Flub A Dub Chub’s. This underground spot will satisfy all your cravings and give you a real taste of Chicago.

Pizza: Deep dish pizza is a Chicago staple! It’s like a normal pizza, but with double the sauce and triple the cheese. We are lucky enough to have a Giordano’s in the neighborhood, that has been awarded “Chicago’s Best Pizza” by NBC, CBS Chicago, New York Times, Chicago Magazine, Chicago Tribune, Chicago Eater, Home & Garden Magazine, Concierge Preferred, and more! Giordano’s is not just a must, it’s a 100% necessary stop to make during your time here.

Italian Beef: Nothing hits the spot more than juicy Italian beef. Traditionally served on a french roll and dripping with au-jus, we know just the place to grab one of these bad boys. Al’s Italian Beef has been crushing the beef game since 1938. Choose your size (regular, big, or jumbo) grab a hand full of napkins, and indulge yourself in one of Chicago’s favorite sandwiches. Many culinary honors have been awarded to Al’s, including Best Sandwich & Sandwich Shop in America, Most Iconic Dish in America, and Top Food to Eat in Chicago Before You Die to name a few.

We put together a dining guide to highlight all the restaurants in our area! Browse through it and find the perfect place to munch at.

3. The Laugh Factory

Opening its doors in 1979, the World Famous Laugh Factory has been recognized as “the #1 comedy club in the country” by such high-profile media as USA Today. There are 6 Laugh Factories in the United States, and the Chicago location is right on Broadway street in the heart of Lakeview East. There are shows 7 nights a week and they are all guaranteed to make you laugh!

Check out the schedule to see what performances are going on during your stay and to get tickets in advance.

5. Catch A Drag Show

Chicago Drag is unique, jaw-dropping, and wig-snatching. Chicago’s LGBTQ+ community Northalsted provides drag shows nightly at a variety of venues. For those who are fans of Rupaul’s Drag Race, we recommend checking out Roscoe’s Tavern which considers itself the home for all things drag race. Check Roscoe’s social media channels to see who’s performing and when! The Kit Kat Lounge is the perfect place to grab some food while enjoying a drag show. They have nightly performances 6 days a week (excluding Mondays) and do drag brunch every Saturday and Sunday AM! Lark Chicago is also worthy of spending some time at. Enjoy a drag show and one of their many delicious cocktails, and check the special events calendar for events like Cher Brunch or Xtreme Bar Bingo. Charlie’s is also a favorite in the neighborhood, open till 4 am every night and till 5 am on Saturdays! There is never a shortage of drag in Northalsted.

5. Spend Some Time at the Lake

Lakeview East also occupies some of the Lake Michigan shoreline.. Take a break from the hustle and bustle of the city and enjoy the relaxing waves of the lake. The AIDS garden of Chicago is a great place to have a picnic and enjoy a walk along the shore. Otherwise, Belmont Harbor and Diversey Harbor are great for unwinding and enjoying the sweet sounds of Lake Michigan.

6. Sluggers World Class Sports Bar

Sluggers is SO much more than your average sports bar. Located across the street from Wrigley Field, the bottom level is a huge bar with a lively dance floor and full service kitchen. The upper level has an entire arcade and even batting cages for use! Participate in some friendly competition and play skee-ball, air hockey, basketball, and a wide variety of arcade games! On weekends and game days, enjoy Dueling Pianos, where talented musicians take requests and play all your favorite hits. Sluggers is one of the most iconic bars in Wrigleyville! Tip: Bring some cash for dueling pianos to be sure your song is next in the line up, it’s a DIY Fast pass to your favorite song.

7. Shop Small, Shop Authentic Chicago

Looking for some art to take home, souvenirs to show off your amazing Chicago trip, or some new articles to add to your closet? We have hundreds of awesome unique shops! The Alley has all your punk rock needs, Amigos & Us is the ultimate Grateful Dead headquarters, and Belmont Vintage Army is a thrift shoppers dreamland. For those looking to take a piece of Chicago home with them, Bob Gally has hundreds of professional photographs of around the city! Women looking for feminine affordable clothing should check out The Colete Collection, and CRAM Fashion has been a chic men’s boutique since 2009.

Check out our retail guide for all things shopping!

8. See A Show

There is no shortage of entertainment here in Lakeview East. We have plenty of venues that host concerts and comedians weekly, The Metro in Wrigleyville, and The Vic Theatre, and many more! Check out the schedules and see a live show! The Mercury Theater has rotating shows and musicals, come be entertained by some of the best performers in town! The Newport Theater is Chicago’s fringe theater, with shows four to five times a week. Looking for some comedy and to get the laughs out? The Annoyance Theatre & Bar always has a jam-packed lineup of comedy shows.

9. Blue Man Group

Blue Man Group will rock your world. Blow your mind. And unleash your spirit. As three bald and blue men explore our world, together we’ll discover music, laughter, and surprises at every turn. By the end of this spectacular journey, you’ll be saying “I DON’T EVEN KNOW WHAT JUST HAPPENED BUT I LOOOVED IT.” The Blue Man Group combines drumming with paint to create a rhythmic explosion of vibrant color. Visit their website for tickets and schedules! Get discounted tickets for families of four, military discounts, and Sunday Fundays here.