Wicker Park offers tons of restaurants and nightlife at a much more reasonable price than River North Neighborhood (aka ballers row). Check out Milwaukee Ave . There's not that many hotels there but a couple really cool hostels that just opened up on Damen Ave . just north of North Ave. You can find tons of hotels in the Loop though. Wicker Park is also located pretty close to many other neighborhoods in case you changed your mind. See West Loop area - There's definitely some hidden gems there as well. Just don't do what most out of towners think is cool and spend your nights bar hopping in Wrigleyville . Check out a Cubs game but end it there.

A couple years ago we stay at the Public Chicago Hotel , in the Gold Coast area. We were walking distance from many restaurants, bars, nightlife, and the metro. We walked to Magnificent Mile and Michigan Avenue .

it was a residential area, but close to everything, and the hotel was very nice.

During the daytime: Michigan Avenue , Millennium Park (the Bean), Lake Michigan , Navy Pier . Cubs game if they're in town.

For evening activities: Wrigleyville , Lincoln Park

Well, the good news is Chicago is the perfect place for male 20 somethings in June - so honestly you can't go wrong with staying in Wicker Park / Bucktown , Old Town or River North Neighborhood .

Old town is great in summer because it's close to the beach, and is a pretty central location to River North Neighborhood and Lincoln Park (Illinois) as well.

Go with Hotel Lincoln - A Joie de Vivre Hotel on Clark, which has a fun rooftop And don't forget to check out the hotels rooftop bar The J. Parker .

The location is also walking distance to Wells Street where you can head to The Fireplace Inn Sports Bar and Restaurant , Benchmark or Old Town Pour House which all have great beer lists, and fun atmosphere for groups of guys.

You're also not too far from public transportation, where you can pick up the CTA - Sedgwick stop that will take you to close by neighborhoods.

As for the beach, although touristy, I'd make it a point for some day time drinking at Castaways . They usually have live music, and it's great for people watching or taking a break from the sun.

You could also make a night of it in River North, although it's a little more in the scene and expensive than other areas. Start at Bub City for some live country music (if you all are into that) and make your way to Untitled for some fancy cocktails or Paris Club for some rooftop dancing. Also, American Junkie is a trendy, fun spot.

As for Bucktown/Wicker Park, go with Big Star for unreal tacos (cash only) and The Anthem is a great sports bar.

If you want a more casual, drinking forward atmosphere, I'd say cruise to Wrigleyville , where you'll find alcohol flowing in all the bars on Clark Street. Moe's Cantina is a good one. Crowd is a bit younger here (early 20's), but something tells me you guys don't mind. :)

Hope you have fun!

Hey Abe, sounds like a good time!

You've got some great suggestions in the answers here -- Jillian killed it (you may just want to pay for her to go and be your tour guide haha).

Below are a few more hotel recommendations. And since I'm a 20-something year old guy as well, I threw in some other recommendations for things I enjoy when I'm in Chicago.

Hotels

If you're looking for something trendy these are the coolest and/or newest hotels in Chicago right now that would be great for you guys.

Thompson Chicago

Godfrey Hotel

PUBLIC Chicago

Acme Hotel Company Chicago

The Langham, Chicago

Trump International Hotel & Tower Chicago

If you end up wanting something more low key (and less expensive) try the Hilton Chicago -- many of the rooms have great views.

I find public transit in Chicago to be pretty good and you shouldn't have an issue getting to where you need to go to/from any of these hotels.

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Once the hotel is taken care of, the next two things I think about when I'm in Chicago are pizza and beer. I imagine you and your buddies will be on my page.

Pizza

You've got to go for proper deep dish/Chicago style pizza. I've been to a few shops that serve this kind of pie (there are a few touristy pizza places you'll want to avoid) and I've narrowed it down to one that I recommend to everyone.

Pequod's Pizza - This place is the real-deal and a local favorite. They're known for their incredible, crunchy and caramelized crust created by baking each pie in decades old cast iron pans.

You can read more about it in this post on my blog.

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Beer

Chicago is a world class beer city. You can easily find a tour that'll take you around to a few breweries, but it's also possible to pick a few breweries and take a self guided brewery crawl.

Here are a few located in close enough proximity to one and other that I hit up on my own self guided tour.

Goose Island Brewpub - The big craft brewer in town. You're probably familiar as you can find their beer all over the country.

Revolution Brewing - this is their brewpub. You can also visit their brewery, Revolution Brewing - Kedzie Brewery & Tap Room, located about 1.5 miles away.

Piece Brewery & Pizzeria - go here last, drink their beer, then oder a pizza or two to help you sober up.

You can read more about these places in this post on my blog.

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Comedy

Chicago is consistently voted the funniest city in America, so a trip to this city wouldn't be complete without catching an improv show at The Second City. You can read more about that in the pizza blog post I linked to above.

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So based on the location of these places on the map, and everyone else's great recommendation, hopefully you'll be able to narrow in on the part of town you want to stay in.

Enjoy!

I would suggest an area called Logan Square which is going through a big transition and its located to pretty much everything. Its close enough to other hoppin areas like Wicker Park and Bucktown , but you can also access neighborhoods like Lincoln Park , and Lakeview on the trains. I am pretty sure though that once in Logan Square, you will enjoy whats there and not wander around all that much. Milwaukee Ave and Logan Boulevard is the intersection that marks where Logan Square is.