Best Restaurants / Things to do in Chicago

@Pierogi Equities Thanks for the tag, I think you listed a lot of really good options. I would definitely echo your comments on the Boulevard Park System as it is really cool and is a good way to spend a summy summer day with a group of friends. Also never seen anyone mention that before, that's a true local's kind of comment. 

Im a bit older now, so I am trying to think back to what was really fun during my intern / analyst years. Half the comments on here are 30-40 year olds recommending $$$ - $$$$ experiences (e.g., Alinea, ugh why recommend an intern drop $1500 on a tasting menu and wine pairing.....). @Pierogi Equities did a really nice job of recommending things that are fun and wont break the bank. Let me try and contribute. 

I think spending a day along the water in Lakeview is absolutely a good time. People will grab a cooler, spikeball, a good group of friends and just kind of camp out along the lakefront. In my opinion, its much better than the overcrowded beaches and is a great way to have a lot of fun on a budget. 

Really fun bars:

1. Slippery Slope just west of Buckton. This spot is a VIBE. Never really been to a bar like it. You walk in and it gives off college bar vibes. You walk further back and there's a huge dance floor giving off some mixture of concert / club / trashy college frat party vibes, and you walk upstairs and its like a semi-classy cocktail lounge. Feels like 3 bars in one. Had some very fun nights there. Not very expensive.
2. Lotties - Another casual spot thats further North but is pretty cost effective and very fun. Good spot for meeting girls too. Warning - it is always packed so if you are looking for a casual spot to chill and have a drink or two, this is not it.
3. Beaumont's - this is a degenerate 4 AM college bar. I have only regrets at Beaus, but it is a critical part of the Chicago experience.
4. Bounce / Joy District / Sound Bar - some fun clubs. These are expensive but definitely worth 1-2 nights out. Drink beforehand, and come fairly lit for a guaranteed good time.
5. Woodys in Old Town - AMongst a sea of bars I cannot stand (The VIG, Benchmark, Pourhouse), there is one chiller bar, and it is Woodys. It isnt as crowded, as loud, or as full of the kind of kids you want to hit in the face, but is still in the center of Old Town. Another good spot to meet girls too. 

Non-Bar Related Activities: 

1. Museums: Check out the Art Institute or the Shedd, especially if you're looking for a good date activity
2. Northern Suburbs - Take the train (or a car) and head up to the northern suburbs. The beaches are 10x nicer, there are tons of spots to play tennis or do other outdoor activities, and the golf courses are really nice. This is where many of the wealthy folks who work in Chicago live, and no one ever seems to recommend exploring it. If you want, you can see the Home Alone house too
3. Ravinia - Another sleeper pick, but this is HIGHLY HIGHLY HIGHLY underrated. Outdoor music venue where its BYOB and you bring a blanket and sit out in a beautiful grassy field and listen to some amazing artists. Really good opportunity to get a mix of guys and girls, a bunch of wine and High Noons, and some good food and make a day of it.

One of my favorite days in Chicago was spent in the Northern Suburbs, so if youre looking for something less focused on drinking and meeting girls, here is what I would recommend. Get a group of 3 friends, go up early and play 9-18 holes (or play tennis on the nice PUBLIC Glencoe grass courts) and then follow it up with kyacking in Lake Michigan, then go to a show at Ravinia.

Honorable Mentions: 

1. Cubs Game - you gotta
2. Cindys Rooftop - Insane spot to get a drink
3. Hange Uppe - Another 4 AM bar you simply must hit. You will see some things...