Best Date Ideas During Summertime Chi

You're going to need this list post-quarantine. Waste no time! Hit all these incredible Chicago spots before it gets too cold!

Let me start off by saying this. There is nowhere like Chicago. Yeah, we don't have the LA weather or the Florida palm trees or the 24/7 commotion like NYC - but Goddddddd, have you seen that view? It's breathtaking every single time I see it and I've been seeing it literally my whole life.

Chicago has so much life, it's truly hard to get bored. I mean not only do we have Lake Michigan for beach days during the summer but we have the incredible city life for post-club grub and Sunday brunches. Here are some great ways to spend your summer days and nights:

Spend the day at Navy Pier. Check their site for special events or shows going on ESPECIALLY during the summer time. You'll find small music festivals, actual concerts, sunset yoga, fireworks and more. If you're not there for an event, grab a slice of Chicago deep dish pizza at Giordano's, ride the famous Ferris Wheel, and go for a stroll making a stop at Crystal Gardens, the insanely beautiful, indoor greenhouse. End your night with some fruity drinks at the famous Margaritaville or Offshore Rooftop Bar for city and lake views.

Address: 600 E Grand Ave, Chicago, IL 60611

@crystalgardensevents @navypierchicago

If you're not in the mood for deep dish, make your way to the Chicago Riverwalk. Pizzeria Portofino has all the views your dying to be around with incredible food (with outdoor or indoor seating). You can't go wrong with lunch OR dinner - they each have a beauty of their own. Once you've inhaled down your food, take a walk along the water. Admire the kayakers, the soothing sounds of the water, and the light breeze as you walk through bright lights and large buildings.

Address: 317 N Clark St, Chicago, IL 60654


Spend a casual night out of the downtown rush and head over to Lakeview. Grab a juicy burger from DMK Burger Bar (#6 is my personal favorite and ALSO THE BEST. Veggie / healthier options available as well!). When you're completely stuffed from burgers and specialty fries, cab (or walk) less than 1 mile to Trickery Chicago. This intimate and low-key magic show is not only mind-blowing but it's genuinely enjoyable - an interactive comedy AND magic show packed in one!


DMK Burger Bar: 2954 N Sheffield Ave, Chicago, IL 60657

Trickery Chicago: 3453 N Halsted St, Chicago, IL 60657

@dmkburgerbar @trickerychicago

Whenever I think of casual nights, I think of either burgers or pizza. Since I've covered burgers, time to cover casual pizza night. In Lincoln Park, you'll find Homeslice. You can't go wrong with anything on this menu. There's options for meatheads AND the veggies. If you enjoy being in an exciting and (comfortably) loud bar environment with GREAT food, Homeslice is your place. Post pizza, make your way to Laugh Factory. There's night shows and there's late late night shows. It's incredible how cheap it is to laugh your a** off for an hour or two. Here's a tip - use Goldstar to get super cheap (and sometimes free) tickets to these shows!


Homeslice: 938 W Webster Ave, Chicago, IL 60614

Laugh Factory: 3175 N Broadway, Chicago, IL 60657

@homeslicechi @laughfactorychi

Need a good weekend brunch spot? 80 Proof has GOT. YOU. Donut wall? Yes please. Fresh omelettes cooked in front of you? Yes please. Unlimited wings? Yes please. Unlimited drink deals? YES. PLEASE. Don't forget about the bomb music and party vibe. Wobble your way on over to a cab to get yourself to Castaways at North Ave Beach. Keep the party going with live music, beach volleyball, and tanning.


80 Proof: 1500 N Wells St, Chicago, IL 60610

Castaways: 1603 N Lake Shore Dr, Chicago, IL 60611

@80proofchi @castawayschi

As mentioned plenty before, Chicago has so much to offer there really isn't any way you could get bored. Day time activities, night time activities - it's endless. Whether you're going out on a date with a significant other or you're planning a girls night out 'date', these ideas will have you ready to go again the next day.

*These are not my images. All images have been taken from Instagram. Instagram handles have been tagged.*


Thanks for stopping by!

I've always been passionate about helping others out! I got you on everything you need -  travel tips, recipes, life hacks, organizational tricks, and so much more. Don't see what you're looking for? Reach out and let's talk about it. Don't forget to check out my About Me page and social media. Let's be friends!

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