Chicago is a great location for a quick weekend trip.  It is very easy to get to from MSY (3 different carriers fly non-stop).  Plus, the flight is under two hours.  We left on the first flight Friday morning (flying United – we ended up getting upgraded to exit row seats for free which was nice) and were at our hotel by 9:00 a.m.

We just took a cab from the airport, which cost around $40-$50…Taking public transportation from O’Hare is supposed to be not too difficult and only $2.50 a person, so that is a definitely cheaper alternative.  Another positive with having a quick non-stop flight, you can leave your destination in the afternoon and still get back to town at a reasonable hour.

There is plenty to do in Chicago to keep you entertained for a long weekend.  There are many restaurants, ranging from the ultra high end to casual joints.  For entertainment, there are plenty of options…Museums, zoos, an aquarium, sporting events, shows, etc.  Chicago also has several Blues Clubs and Piano Bars for night activity.  We were pretty busy while we were there and still did not get to do a lot of stuff I would have liked to have done.

On transportation, I would not recommend renting a car.  Parking is outrageously expensive with most hotels.  The public transportation system and cabs should get you around just fine for a good bit less than you would spend renting a car and driving (unless you want to go to some of the more out of the way places).  Though, if you do decide to rent a car, driving did not appear to be near as crazy/hectic as it is in New York.

I really like the time we went (May).  For several days the weather was unbelievable.  The other couple days, there was a “heat wave” which was no worse than your average day in May in south Louisiana.  It does supposedly get pretty hot in Chicago in the heart of summer, as well as getting very cold in the winter.  So, I would try to go during the spring or fall.  That said, I’m sure anyone would have a fine vacation in the summer/winter.

Hotel

We stayed at the Park Hyatt.  I got a really good rate there through a best rate guarantee (note: you can also get a pretty good rate through the ABA).  I also have some Hyatt status perks that made it worth our while to stay there.

It is a very nice hotel (upscale rooms, good “service,” etc.), but I would not pay full price – or close to it – to stay there.  I still take the philosophy to not go overboard on the accommodation on these quick weekend trips because you are barely in your room anyway.  Breakfast at the hotel restaurant (Nomi) was included in our rate and was excellent.

I did really like the location of the hotel – Michigan Ave./The Magnificent Mile.  Though, Chicago is a pretty walking friendly city, so anywhere in the downtown/magnificent mile area would probably be good.  The Park Hyatt was a little further North on Michigan Ave. so that gave us more opportunities to walk to more places on that side of the city that we may otherwise not have walked if we were staying on the downtown side of the river.

Entertainment

We did a lot of walking around and seeing the city on this trip and really enjoyed that.  On our first day, we just walked around the Magnificent Mile and Downtown areas and easily killed a couple hours.  That afternoon we did an Architectural River Cruise through the Chicago Architecture Foundation (there are many different organizations offering tours).

We liked the tour, especially doing it the first day.  It kind of gave you an overview of the city and made you pay attention to things that you probably would not have during your time in Chicago.  I liked the organization we did the tour with…but really, I have nothing to compare it to.  Also, we did not pre-buy a ticket.  This does not seem like it would be necessary except for the busiest times on crowded days.

The second day, we walked from our hotel down State St. to Lincoln park and eventually to Lincoln Park Zoo.  Walking down State St. was a very nice walk.  You walk through what appeared to be an older residential neighborhood with lots of trees and some very expensive looking homes…Alyce was ready to move into one of them.  Walking through Lincoln Park was also a nice walk.

We spent the majority of the day at The Lincoln Park Zoo.  It is completely free and kept us entertained for the better part of a day.  The Brookfield Zoo is supposed to be nicer (coming from a guy I work with who grew up in the Chicago area), but it is way more out of the way and not free.

The third day (Sunday) we slept in and ate brunch at the hotel.  After that we walked to the Goose Island Brew Pub for a tour.  The “tour” was pretty minimal.  They walk you in to the brew room (for the pub’s craft beers) and pretty much explain the process of brewing…no real tour since this is the pubs brewery and not the main brewery for the beer.  That was ok.  Next you go in to a room in the bar, and they walk you through a tasting of 6 of their craft beers.  This was definitely more interesting than the tour portion and worth it.  Overall, I certainly wouldn’t plan my trip around doing a tour at this place, but it is something fun and different to do.  If you do go here, leave yourself some time after the tour to hang out in the pub and try some more beers.

…And a note on walking to the Goose Island Pub.  I would recommend against it unless the weather is very nice and you are in the mood for walking.  It is far.  Also, the scenery is nowhere near as nice as the walk down State St. to Lincoln Park, but you do get to see more of the residential areas of Chicago, and a nice church or two, etc.  Plus, we decided to do this walk the day the heat wave came through, so it was hot.  I survived the walk ok, but I think Alyce was about to pass out by the time we got to the pub (and was none too happy with me).

On our final full day, we went to a Cubs game.  I highly recommend catching a Cubs game if there is one when you will be in Chicago.  Neither Alyce nor I are big MLB fans, but we really enjoyed going to the game.  Plus, we went on Memorial Day, so there were some extra activities associated with that (an eagle flew to the pitchers mound from the scoreboard in center field at the end of the national anthem).  Taking the train to the stadium is plenty easy.  Also, we sat in reserved seats, but the outfield general admission seats are supposed to be lots of fun and have more of a party like atmosphere.

That evening we walked back to Millenium Park and saw Buckinham Fountain, as well as the fountains with the faces on them that spit water out.  It was a relaxing way to end the day/trip.  On the morning of our flight, we walked down Michigan Ave. one more time to catch anything we missed.

We did a good bit over four days, but there would still be a lot that I’d want to do in Chicago…Go to the aquarium, go to the Museum of Science and Industry, check out one of the Blues Clubs or one of the improv comedy places, maybe even check out a show depending on what was playing at the time, etc.

Food

A lot of the highly regarded restaurants book up early in Chicago…We made firm plans to go to Chicago about 2.5 months before our scheduled dates and several of the places we wanted to go were already booked up.  Our way around this was to get to places early (5:30ish).  This worked out fine for us, as we do not mind eating early and did not have to wait to eat a single time.  Another option to avoid waits is to eat lunch at the restaurant.

Our first day for lunch, we ate at Frontera.  Frontera is a Mexican restaurant by the chef Rick Bayless.  It does not take reservations at all, so if you want to go for dinner no one there will have reservations.  Topolobampo (Bayless’s “nicer” restaurant) is in the same building.  You actually go to the same hostess and they ask what restaurant you want to eat in…It is quite confusing why there are even two separate restaurants.  Either way, the menus do not seem to be too different.  We got to Frontera about 15 minutes before it opened for lunch; and, although there was a line when we got there, we made it in for the first seating with ease.  That said, it is a pretty big place and they seem to move people in and out at a pretty good pace (though you are certainly not rushed with your meal).

Frontera’s menu is large and gives the options of ordering small plates or a more traditional sized entree course.  We went with 6 small plates, which was a lot of food.  It was all very good and lived up to the hype.  This is true Mexican food, not the Tex-Mex stuff you find at most “Mexican” restaurants.  The prices here were extremely reasonable.  We had two margarita’s, stuffed ourselves with food, and still spent just over $100 (tax and tip included).  Just remember the potential downside to eating at a popular restaurant with reasonable prices…You can have some idiots next to you.  We had two people next to us who did not eat pork and did not like spices – and were loud/obnoxious about it.  I almost turned and asked what the hell were they doing there if you knew you weren’t going to eat the majority of what’s on the menu, but I refrained.

That night for dinner, we went to 676 Restaurant in the Omni Hotel.  Our plan was to eat a small dinner after a large lunch at Frontera and just eat lots of meats and cheeses with some wine.  Well, that turned in to more food than we expected, which was ok because the meats and cheese were excellent.  The meats are cured in house (they showed is the curing room after we ate) and the cheeses were very good too.  I can’t comment on any of the other stuff there because we did not try it, but they did have our favorite meat/cheese platter of the trip.

The second night we ate dinner at Lou Malnati’s (a Chicago style deep dish pizza place).  We really liked it; they are supposed to have a more “buttery/pastry like” crust…Whatever it was, it was good.  But I’m sure any one of the main 3 pizza places (Lou Malnati’s, Gino’s East, and Giordano’s) would probably be very good.

The third night we ate at Girl & the Goat.  This was probably our favorite place of the trip (by just a little bit).  It is another reasonably priced small plate style restaurant.  The owner/chef is Stephanie from Season 4 of Top Chef (she won).  We liked all of the courses here, but our two favorite courses of the entire trip were probably the beef tongue and the octopus we had there.  If anyone eats here and is feeling adventurous, I highly recommend those two courses.

Girl & the Goat does take reservations but appears to book up extremely early.  That said, we got there around 5:00 and were sat down with no wait…Though they did tell us we would have to be finished by around 6:30 – which was no problem at all unless you are planning on having a very leisurely dinner.

Our last night we ate at The Purple Pig.  This is yet another small plate style restaurant that was very good.  They do not take reservations here, so everyone is in the same boat with getting there and having to wait a little bit.  We got there around 5:30 and were sat down immediately at a table for two…Speaking of which, several tables are “family style” meaning one long table with several different groups sitting there, so be aware of that.  It is not as bad as it sounds, but it is still not really our style.  They do have a good bit of tables for two, you just may have to wait a little longer to get one.

The food here was very good too.  We tried cuddle fish, which was surprisingly good and very similar to calamari.  One other plus for the Purple Pig is its location.  It is located within easy walking distance of just about any hotel a tourist will be staying in.

One place we wanted to try for lunch but did not make it to was Pastoral Artisan Cafe…We just did not have the time and weren’t always hungry after a big breakfast.  Next time…

If anyone is still reading at this point, it should be obvious we really liked Chicago.  It was a very easy trip (travel-wise).  Many things were pretty reasonably priced with the trip, and the city is great for a long weekend getaway.