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Long weekend trips really are the best. Take off work on a Friday, hop a flight someplace cool, and try and do everything possible to forget that you’ve got work on Monday. So two weeks ago, when I saw ridiculously cheap airfare to Chitown, I thought hmmmm, why not make this our first “Trip’n Tuesday” feature in a while? I mean, it didn’t hurt that it was also the Bear’s home opener, maybe I could get tickets. So here it is, my 72 hour travel experience in Chicago and a few of the can’t miss items the Chi has to offer:


Listen just like everyone else, you may front like a baller at times, but at the end of the day no one wants to drop crazy money on flights for a 3 day weekend. I used to check my flight costs. Because it literally searches every travel site out there, as well as the airlines direct pages, it always gives you the best pricing options. 10 minutes after searching NYC –> Chi, I was booking non-stop flights from La Guardia to O’Hare for $173.


While there are 3 airports in the NYC area (LGA, EWR, & JFK), I prefer flying out of LGA for short trips specifically because of the transport options. The airport is a flat 25 minutes from almost anywhere in NYC, it only costs between $30-40 to take a cab there, and I’ve found the security lines to be the shortest of the 3 airports. If I’m going away on a longer trip, I’ll choose any of the 3 airports, but on a short trip it’s all about speed and value.

When arriving in Chicago, you can absolutely take a cab, it’s about $45-60, but I prefer taking the blue line for the following reasons. Firstly, traffic into Chicago on a weekday can be absolutely mad. While the trip should only take about 30minutes, it can take 2 hours if you hit any kind of rush hour. The blue line runs literally from under the airport directly into “The Loop”, which is the center of downtown Chicago, for only $5. Not to mention it only takes 40 minutes, so you’re only losing about 5 minutes.


Now, picking a hotel in Chicago is like picking one in NYC. In some cities, like Miami or Vegas, your hotel is EVERYTHING. It’s literally where you spend a majority of your time, and being at the right hotel definitely determines how good your social life is going to be. However, in cities like NYC and Chicago, you want a quality hotel experience, but it’s really all about the location. You want to be close to transportation, and nightlife. But let’s be honest, we all still want to stay in a dope hotel.

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Before picking my hotel, I called my friend Rob, who has run sales and marketing for some of the coolest hotel chains in the world. Rob briefed me on the River North District, and recommended me the Hotel Sax for my weekend. After checking out their website ( I called Rob’s friend Gully Nassiri, their Director of Sales, and booked my room. There are a few other great hotels in Chicago, that are young, cool and beautiful. However, the combination of price, location, and quality that the Hotel Sax provides, definitely makes it the best hotel for a young traveler, looking for a high-quality but fun weekend. The Hotel Sax is right next to the House of Blues on Dearborn and is only a a block in any direction from some of the best bars, restaurants, and clubs in the city. The rooms are big, and have a really well designed retro/madmen feel. In an accompanying post you can see my full breakdown on the Hotel Sax. Another big advantage is their concierge is super hooked up, and made sure I had reservations and vip access to the best spots in Chi.

My Top Hotels Choices in Chicago: (Based on price, style, room size, and atmosphere)

  1. Hotel Sax
  2. The James
  3. Palomar Hotel


Chicago has a great food scene, both on the high-end dining experience and for quick bites. On a weekend trip like this, I like picking two great restaurants and having amazing dinners both nights. Now, I am all about gourmet food, but at a price that FITS the meal. Like most of us, I am fine spending $300 on dinner for 2, IF it’s worth it. But overall, when going out on a Friday or Saturday night, you’re looking for great food but also a great atmosphere. After speaking with a bunch of my Chicago friends, I settled on RPM for dinner on Saturday night and you know what? It blew me away.


RPM is a celebrity restaurant, owned by Bill and Giulianna Rancic, which usually spells overpriced average food, and very cheesy/trendy vibe. I openeing-2_18a_12-278-fb1-624x416couldn’t have been more wrong. A contemporary italian restaurant in the heart of the River North area (only a block from my hotel), RPM is one of the hottest spots in Chicago, and well worth the buzz. They are so popular, I had to go through their PR department to even get a table on a Saturday night! So make your reservations in advance (if you’re staying at the Sax just ask Catherine, their head concierge, to set it up for you). However, Anna in RPM’s PR department, made sure I had a 9:30pm reservation for 2 (prime time for Chicago, which is a little bit earlier of a city than NYC), and it was on. From the moment you walk into RPM the mood is set – the crowd is younger (I’d say 25-50), stylish, and cool, the music is DJ’d, and the decor is modern, but tasteful. My date (you know I had to have a beautiful girl with me to eat at spot like this) and I grabbed a drink at the bar first, before the hostess brought us to our table. The service, food, and drinks were great. The restaurant also easily accommodated my friend Kelli and her husband Tim who joined us at our table after dinner for a glass of wine. All said and done dinner for 2 plus a couple extra drinks for Kelli and Tim was under $200 – and as I said the food was amazing. Chef Doug Psaltis absolutely killed it with this menu.

My Top Restaurant Spots in Chicago: (Based on going out Fri/Sat, atmosphere, food, and price)

  1. RPM Italian
  2. The Girl & The Goat
  3. Sunda

Great post by RUDMA in the wake of today’s terrible shootings in DC: 500 or less – We need to see some good


Ok so I only really went out one night, because I had a ton of work to do, but everyone kept telling me I had to check out the new Underground. While there are a few other spots that really jump off, Underground is definitely the spot right now. Run by Rockit Ranch Productions, who pretty much own the Chicago nightlife scene, Underground is right next to RPM. We got there at about 12:30am, and the line outside was crazy, and Martin, who was working the door, was being strict on the door policy (even turning down groups of hot girls who weren’t on the list). However, again, Catherine at Hotel Sax, hooked it up and made sure myself and my date were on the list. We went right in, down the stairs, and into this awesomely designed club. It has this 1920’s/Gatsby feel that is really well executed. Which is actually nice to see after partying in NYC for so long, where yes the music and atmosphere is great BUT there is no attention put into design anymore. There were two rooms, both of which were packed, and the sound system and lighting wall were really high quality. The crowd was good looking and fun, with a great girl to guy ratio. Everyone was partying and really wild’n out. There are a few other hot spots in Chitown worth checking out, but Underground is definitely my favorite club spot in Chicago.

My Top Club Spots in Chicago

  1. Undeground
  2. Paris Club
  3. The Board Room

Day Drinking/Brunch

If this isn’t everyone’s favorite part of a weekend, then I don’t know what is. Chicago is a really fun drinking city, and with it’s massive sports culture, the bars and restaurants are packed on football Saturday’s and Sundays. I went bar hopping all over Wrigleyville, a popular area of Chicago to live in for young professionals, Lincoln Park, and River North throughout Saturday and Sunday. Racine Plumbing and the Kerryman were my home for the Irish Game, and it felt like just the type of spots that you’d want to watch the game. Guinness and Jameson were flowing like… well like Guinness and Jameson at an Irish Pub. Nellecotte, Belly Q, and Rockit Bar all have great brunch scenes as well, with great food and the traditional bloody mary/mimosa drink specials. But for Sunday Football, I found my spot in Chicago. Like a mexican version of the NYC club/bar Bounce – El Hefe is the spot for Sunday Funday. Hot bartenders, bottle’s poppin, beats pumpin and fake mustaches all over the place, El Hefe was the shhiiittt on Sunday afternoon. I’m not even going to rank my day drinking/brunch spots, because based on what I’ve seen and heard there are just so many more spots to check out, I’d be doing an injustice by picking any just yet. But for now I’ll just say that El Hefe definitely is the spot I’d go back to for my Sunday Funday in Chitown.


Sports and Activities

Ok in case you didn’t know, Chicago is a DIE HARD SPORTS TOWN. Baseball, football, basketball and hockey, this city lives and dies with it’s sports teams. Being as it wasn’t basketball/hockey season yet, the only two things I had the opportunity to experience were the Cubs and the Bears. And by using the word only I’m being completely sarcastic. Going to Wrigley field for a cubs game is an absolute must for any sports fan at all. Even though the cubs are an absolute mess, and the MLB totally fucked over Chicago by not letting Cuban buy the team, Wrigley is an american institution. The ivy, the brick, the rooftop seats, going to see a game live is amazing. The stadium is big, and yet you feel right on top of the field. The stadium is old, and yet it doesn’t feel dated. If the Cubbies were even half-decent, there wouldn’t be an empty seat in the house. As it was, the stadium was still 80% full for a Saturday day game vs. the Brewers.


Now, 75% of the reason I wanted to go to Chicago was to see a Bears game. Not sure how many of you remember the SNL Sketch, Da Bears, but Soldier Field, Beers and Brats are what I picture when I think football. I got tickets at the last minute via the NFL Ticket Exchange (a highly underrated site if you don’t know about it), and took my friend Alli with me to the game. Aside from the 20minute walk from the train to the field, everything about the gameday experience is great. The fans, who by the way engulf the entire city on Sunday, are passionate, rowdy, and in a good way – totally hammered. It’s a great drinking culture, whereby the fans are getting sauced up but having fun. For as much as I love my Eagles, I have to admit Phila is a drinking culture but with more of an anger/edge. Chicago is energized but with a slur, and I loved it. The game, vs. the Bengals, was great with Da Bears, making a late 4th quarter comeback at the hands of the insufferable Jay Cutler. Who, by the way, even when he’s winning, may be one of the most annoying people I’ve ever encoutered. Doesn’t he look like he’s got a touch of down syndrome? Ha. But I digress. The game day atmosphere was great, and because they are an hour earlier than the east coast, it was only 2:40pm when the game was over! This meant there were like 8 more hours left to our Sunday Funday (which is right when we headed over to El Hefe).


Overall Review:

Chicago is an awesome city that I wish I had travelled to more during my 20’s. It’s big but small (in the sense that it’s easy to get around and know the scene). The people are friendly, cool, and educated/ambitious. While it’s not LA or NYC, people are good looking and fit – which is not always the case in midwestern cities. The city is really affordable, but still has class, edge and energy of a major east coast city. The museums, architecture, food, nightlife, and sports cultures give the city a vibe that a New Yorker can appreciate and a 25 year old can totally take advantage of. Listen, if you want fun 3 day weekend I highly recommend Chitown. Except, maybe go in October or November when the NBA and NHL are in season as well, but before it becomes FREEZING in the winter, which it will.



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