A Weekend In Chicago


If you are looking for some fun in the sun during the day, a bit of culture during the evenings and a splash of comedy, Chicago is the place to be. The best time of the year to go is around the summer when you don’t have to wear 200 layers of clothes.

We stayed at the Affinia hotel, which I would highly recommend. It is located at the heart of town (the equivalent of New York’s 5th Avenue), where you have close access to Millennium park and the Lake Shore drive. Though the view is lacking, the rooms are spacious and there’s a sunken bedroom floor which adds the luxurious feel of the hotel. They also provide you with an iPod Nano, walking tour cards and numerous other goodies for the weekend (at your request).

We kicked off the weekend by engulfing a deep dish pizza from Gino’s East of Chicago. Our friends thought it was absolutely fantastic, though my taste buds got overwhelmed by the tomato sauce and generous serving of cheese. Take note that the line to the restaurant is generally long, so I would check with the hotel you are staying at for an “express pass” which provides you with a faster avenue to the food!

After gorging ourselves, we took a stroll down to Millennium Park where we came face-to-face with the infamous Bean (whose official name is “Cloud Gate on the AT&T Plaza”, though “the Bean” sounds better). It is a gigantic stainless steel sculpture in the shape of a bean that shimmers the cities’ skyline. On a nice day, it is flocked by people take photographs and what not. From here, you can venture down to lake and take a leisurely stroll along the lake or you can head to one of Chicago’s giant skyscrapers.

Since the wait at the Sears Tower is apparently long and the tower itself is a little out of the way from Millennium Park, this meant that the next stop was the Hancock Tower. After 15-20 minutes in a line, you can stand on the 90-something floor and absorb the break-taking 360 degree view of Chicago. It’s the perfect setup for the next day activities because you get a good layout of the land.

The evening activities started with dinner at Bice Ristorante, a chain restaurant, which wasn’t much to write home about and then transitioned to Andy’s Jazz Club, where for a $15 cover you get to enjoy music from Chicago’s top local talent or world touring musicians. If you are a hardcore jazz fan, however, we were told that you should venture further north of Chicago (about 30 minutes) to Green Mill. We didn’t make it out there because Green Mill is supposedly the only attraction in that neighborhood.

Day two should kick off a river tour of the city run by Chicago Line Cruises (the Architectural River Cruise). Onboard the boat, you will get some free pastries for the morning and are accompanied by a delightful narrator whose knowledge of the city’s architecture would rival the repertoire of a college professor. It’s definitely a great way to get more appreciation of Chicago’s diverse architectural landscape.

From the cruise, we trekked up north to what I thought was the highlight of my food experiences in Chicago. A small family-owned joint called Flub-A-Dub-Chubs serves up “Chicago Style” hot dogs. Served with an army of toppings including cucumber, tomatoes, pickles and relish, these dogs are delicious and to be shoveled into your stomach without ketchup (though ketchup for the fries is perfectly acceptable).

After scoffing down both a flubby and a chubby, renting a bike from Bike and Roll is perfect way to kick off the rest of the day. We started from the Millennium Park Bike and Roll (there are several locations) and headed south towards the Planetarium. But, we would recommend heading north towards the Navy Pier and further up to the beaches (North Avenue Beach or Oak St Beach) where you can stop off and have a couple of drinks and relax in the sun.

Once we were done with the bike riding, we headed over to Bistrot Margot, a French bistro that was located near the comedy show we were going to. The dishes were everything you’d expect from a decent bistro with healthy portions that are not over-flavored, but very delightful. It is definitely not fine dining, but great value for money. Bistrot Margot is also conveniently located near the Second City comedy club, which we think is an absolute must when in Chicago. The impromptu performances and rehearsed skits were absolutely hilarious and witty and made the audience fall out of their chairs the whole night.

So, all in all, it was a great time, but there are a couple of things to note. We ventured out to Hot Dugs (which is apparently the #1 hot dog joint) only to discover that it wasn’t open on Sundays, so I would recommend you call ahead before forking out the $20 cab ride. Also, if the weather was warmer, renting a bike earlier in the day and spending all day on Lake Shore drive is the way to go. Finally, the one thing that we didn’t get to do was head out to Wrigley Field for a game at one of the oldest and most iconic baseball fields. The Cubs weren’t playing that weekend, but this only means one thing… another excuse to go to Chicago!

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