
My husband and I recently took a short weekend trip to Chicago. It was our first time really visiting there as tourists, so we took time to do all the classic touristy stuff. I wanted to share with you our travel successes, as well as our pitfalls and things we will do differently next time — I hope this is useful to some folks out there, and I ask other experienced Chicago travelers/residents to please add your experiences, tips and advice in the comments section!
Transportation
We began our trip with a ride on the train, from O’Hare Airport to our hotel. It was an easy enough way to get to our hotel, and certainly the most economical (our tickets were $2.25 each). The CTA has a good website so you can check out maps of the system before your trip, allowing you to make a note to yourself what train to use, where to transfer, and what stop is closest to your destination. Because I like to err on the side of over-prepared, I even printed out a map from their website so I could have it with me when we arrived. However, I’m sure there are maps in the subway stations if you don’t want to do this.
When buying a CTA pass, keep in mind that they can be used on trains as well as buses. If you plan to use buses while in Chicago, you may consider putting $10-$20 on your CTA pass at the beginning of your trip so you don’t need to refill it again during your vacation. We ended up having a few extra dollars left on our card, and just passed it along to a friend that would be visiting the city soon.
The ride from O’Hare to our hotel on Michigan Avenue and Harrison Street took about 40 minutes. If you’re not used to train/subway travel (as we are not), you may be surprised at how loud the train is. It seems to me that the “L” is louder than subway systems in other cities – but it has admittedly been a few years since I’ve ridden any other subway, so perhaps I’m not the most reliable source. Nevertheless, it is too loud at times to visit with the person next to you, so I suggest bringing some reading material or an iPod to keep you occupied on the ride.
Once we were in the city, we utilized the bus system rather than the subway. I guess we liked being able to really take our time and look around as the bus was traveling. Figuring out the subway system is much easier than figuring out the bus system, but a tool that helped us extraordinarily is the functionality on Google Maps to get directions via public transit. It was so awesome! Of course, we didn’t realize this existed until our last day in Chicago, but even then it helped us so much. We have Droid phones, and so we tend to use the Google Maps app quite a bit when traveling, and by simply clicking on the “public transit” option when getting directions, you can see what subway line you should take, or what bus number you should take, and what stop you should get off on. To find this functionality, simply log on to Maps.Google.com and click on “get directions,” enter location “A” and location “B,” then select the “public transit” button – next to the “car” button, which is the default.
Lodging
Because we are always trying to cut expenses while on vacation, we generally try to get the least expensive hotel room in the most desirable location. In this instance, that meant staying at the Travelodge hotel near at 65 East Harrison Street, just off Michigan Avenue by Grant Park. The location was great – very convenient. However, that is where the positive attributes end. We regretted our decision to stay here – our experience was so bad that it was not worth the money we saved. The “free breakfast” they advertise is really a few pre-packaged pastries and dried-up bagels, and our first day there, they RAN OUT OF FOOD by the time we got there. So, you need to go down before 8 a.m. if you’re going to get the complimentary breakfast. Of course, if they run out they conveniently have breakfast food you can purchase. Definately smelled like a scam to me. However, there is a Dunkin’ Donuts across the street, and that proved to be a good spot to start the morning.
The rooms were dirty and the maid service was horrible. They didn’t refill our toilet paper ONCE during our stay and by the time we left it was all gone and we were using kleenex. We also had to call down for additional towels each day because the maid would leave enough for only one person. The carpets were very, very dingy and it was pretty gross walking on them with bare feet. I forgot my hair dryer and got one from the front desk and the heating element didn’t work. It was all par for the course at this exceedingly below average hotel. We booked through Travelocity, and our rate was approximately $120/night. For $50/night more, we could have had a very comfortable room in the same area with the normal amount of cleanliness and comfort we are accustomed to. For us, it would have been worth it – but everyone’s travel budget and standards are different!
Activities that are free!
My husband and I are not hard core athletes, but we do both run a few times per week in attempt to stay in shape. We started off both mornings with a run along Lake Michigan. Both of us agree that this was probably our favorite part of the trip! In the mornings, the air was cool, and we were able to explore the lake shore on foot. Because our hotel was located near Michigan Avenue and Harrison Street, we were able to run through Grant Park, which was less than one block from our hotel. We ran through Grant Park and over to the Museum Campus of Chicago, where the Shedd Aquarium, Field Museum, Adler Planetarium, and Soldier Field all reside. It was a gorgeous run, and the view of the skyline as we ran back towards Michigan Avenue and our hotel was amazing. Even if you’re not a runner, I highly recommend at least taking a morning walk along this route. The view cannot be beat – and it’s free! Parts of the path are a bit isolated, so I would not recommend this path for nighttime.

Our first full day in Chicago we took in most of the Magnificent Mile – all on foot. This was a great way to familiarize ourselves with the tourist hot spots of Chicago, get some good exercise, people watch, and take in the sights. We were able to window shop at many of the shops that line the Avenue (I was really good and only went into a few stores, and only bought one shirt the entire time we were there! Regardless of whether you are browsing to buy or just browsing to browse, the shops on Michigan Avenue provide lots of fun – and possibly free – entertainment). We even stumbled upon a few gems – like the courtyard of Fourth Presbyterian Church, located right on Michigan Avenue, like an oasis of calm amidst all the chaos. It was a great place to stop and rest our weary feet, and get away from the crowds for a bit. The inside of the church is a gorgeous place to sit and reflect for a few moments.

Along our walk we passed through Grant Park, Millennium Park, and Lincoln Park – all gorgeous tourist spots and all free!! We grabbed a Chicago-style hot dog at Millennium Park for lunch, and ate underneath a tree with a gorgeous view of Cloud Gate, the big silver bean sculpture. We also took in the zoo while at Lincoln Park, which is also free. Between Millennium Park and Lincoln Park, we took in lots of sun along the beaches of Lake Michigan, right off Lake Shore Drive. This was great for people watching and ice cream eating, but both of us wished we had thought to bring our swimsuits. It never occurred to us that we would have the opportunity to relax on a beach during our stay in Chicago!
One thing I do not recommend is walking this entire distance in one day, especially in the heat of the summer. This is what we did, and it was way too much. We totally wore ourselves out, and by the time we reached Lincoln Park, we were exhausted, hot, and crabby. We figured out the bus route from there and rode the bus back to our hotel room to take a much needed nap before venturing out for dinner that night.
That night, we realized that we would not have the energy to do both the Field Museum and the Art Institute of Chicago, so we made a decision. After having dinner at a restaurant near the Art Institute, we simply strolled inside the museum to take in the beauty of the lobby, and to peruse the gift shop. We had a good time looking at all the merchandise displaying the works of art that are found inside the museum, and felt satisfied with that. Granted, this likely sounds absolutely horrible to some of you art-lovers out there, but understand that I had been to the museum twice before, and my husband, who had never been there, is really not a fan of art in the first place. So, for us, this was sufficient due to the fact that we really only had time to properly explore one museum, and for us – the choice was the Field Museum.
Activities that are not so free
We spent the majority of one entire day wandering around the Field Museum. We bought the all-access ticket to all the special exhibits and the 3-D movie, and we thought it was very interesting and fun. If you have kids, I think this would definitely be a great place to visit, but my husband and I had fun looking at all the exhibits – those designed for adults as well as children. The only negative experience we had at the museum was buying lunch at the Corner Bakery that is located inside the museum. Other locations of this chain may be great, but this one was less than impressive. The food was not tasty enough to warrant the high prices, and the organization of the cafeteria-style order and pay line was horrible. Just managing to get our food and find a table proved to be a very stressful experience. I can only imagine doing it with a few kids. My recommendation would be to bring something to snack on in your purse/travel bag, and go outside the museum at lunch time and have a picnic on its front lawn, which overlooks Lake Michigan. The view is beautiful, and the entire experience will be much more serene. Keep your original ticket, and they’ll let you back inside after your picnic.
One of the most enjoyable things we did while in Chicago was go out for a nice dinner along Michigan Avenue. By using www.TripAdvisor.com, we were able to search for a nice dinner spot based on location, type of food served, and even price range. This is how we came across Bandera Restaurant. A quick Google search led us to reviews of the restaurant, which convinced us that it would be a good choice for us. The food was great, and since it was a Saturday night, they had a live jazz band playing – what’s more Chicago than that? It was a great experience. A little research in our hotel room before we left proved to be a great idea. One reason I highly suggest taking along a laptop when you go on vacation if you have access to one!

Other activities I would recommend
There are, of course, tons of great things to do in Chicago, and a weekend is simply not enough time to do them all. I wanted to highlight a few things that we didn’t have time to do on this trip, but will definitely be on our to-do list for our next trip to the Windy City.
We had read fantastic things about the Museum of Science and Industry, and my husband was really excited to see the place. However, we quickly realized that a short weekend trip was not enough time to see more than one museum – especially if you had some things you wanted to do while in the Windy City other than stand inside a concrete building all day! However, now that we’ve seen the Field Museum, I don’t think we’ll feel the need to visit it for several more years. So on our next trip to Chicago, we will definitely make this one destination of choice.
We also found out about a cool touristy activity while in Chicago that we did not take part in – Segway Tours of Michigan Avenue from Navy Pier. This would have been a fun – and less tiring – way to see many of the sights we saw on foot our first day. If we had known about this beforehand, we likely would have splurged and taken part in the tour. Neither my husband or I have ever ridden a Segway, but it seems like the kind of thing we would like. It’s always fun when you can inject a little adventure into your regular, run-of-the-mill sightseeing day.
The one thing we regret about our trip to Chicago is that it was so short, and that all our time was taken up by checking out everything there is to see and do along Michigan Avenue and the lake front. We weren’t able to get out into the rest of the city and check out any of the very cool neighborhoods that Chicago has to offer. Next time, I definitely would like to take advantage of one of the many walking tours offered as a way of exploring other areas. The link I’ve posted is just one company that offers such tours – but do a little digging online and find a tour that specializes in something you love – architecture, history, food, etc.
Your turn!
So – for everyone out that that has visited Chicago before, or who has ever lived in the Windy City, please share your expertise and let us know one or two must-see’s while visiting the city!