Don't rent a car. First of all, the streets are very busy and traffic can get pretty bad. Second, if you're staying at a hotel, you should check to see if there is parking, because not all hotels offer it. If there is parking, the per day charge will be steep. The Hilton we stayed at was charging $23 per day, so we figured we didn't need a car that bad. Use public transportation. Most of the places you'd want to go are probably on a Chicago Transit bus line. It's a cheap way to get around, and pretty reliable. Cabs are expensive. If you've gotta use one, they're easy to get, but boy are they expensive. If you're with other people, it's a better deal-you can split the cost. They'll get you where you need to go, but $20 for a ride from the Hilton to Navy Pier was a little steep. Trolley and bus tours aplenty. Another way to go is by trying one of the many trolley tours there are. There are many different companies that offer trolley tour service, stopping at all the important sights. Most companies have many trolleys (or buses sometimes), all going the same route, and for about $20 you can get on and off all day as many times as you like. These are more reliable than the other service we tried, which was a free trolley service run by the city. It's a great idea, but there are about 5 different routes, making it inconvenient having to transfer to a different trolley a couple of times depending on where you want to go. What makes it more inconvenient is that they don't run very frequently. On Saturday, the one we waited for said it only ran on the half hour. Murphy's law is that the one you will wait for will take 29 minutes, because you know the odds are that one has left the stop just before you got there.
Where to Stay
There are lots of nice places to stay. We stayed at the Chicago Hilton and Towers and it was very nice. It's an old hotel, but has been renovated, so the public areas still have the charm of a big old hotel, with a beautiful lobby, while the rooms are up to date. They're plenty big, and some have 2 bathrooms. Try to get a room with a good view-because of the design of the hotel, you could end up looking at another part of the hotel rather than have a nice view of the city. We got there at 9am and they had a room for us to check into, so they're pretty flexible about check in times. The workout room isn't free-the daily charge isn't worth it. The pool is supposed to be free, but we noticed a $10 charge on our credit card for the one time we went there, so be careful and make sure they don't charge you if you're only using the pool.
What to Do
Museum of Science and Industry A cool museum.
Navy Pier Overrated. Way too crowded and the traffic getting in is a nightmare. We took a cab there and we spent a half hour stuck in the traffic trying to get to it. Once there, we were quite underwhelmed. There is a shopping area, with some o.k. gift shops, but nothing to write home about. The restaurants have too long a wait to bother, so McDonald's could be where you end up if you're hungry, and even that was extra crowded. One of the few bright spots included the ferris wheel, which is pretty tall and has a great view of the city (except that a nearby building blocks the view of the Sears Tower). The other bright spot is the fireworks display that goes off every Saturday in the summer at 10pm. If you want to see the fireworks, be sure to reserve a good viewing spot early-it gets packed fast. Overall, though, it's not worth the hassle to get to the Pier.
The Sears Tower Until recently, the tallest building in the world, until a taller one was built in Kuala Lumpur. Be prepared for a long line to get in, but the wait is worth it. The view of Chicago from the top is spectacular. Don't come here hungry, especially on the weekend. There isn't really any food in the area that's worth it-Sbarro pizza is the only place in the building nearby the entrance to the exhibit. Yuk.
Where to Eat
You'll notice there's pretty much only restaurants in our hotel, and restaurants in Marshall Fields, with one exception. We were only in the city for a weekend, and the other places we were at were a bust as far as nice stuff is concerned. The Museum of Science and Industry has a cafeteria, but it looked yukky, so we opted for the Pizza Hut. We also went to Navy Pier expecting to find a good place to eat, but the waits at all the restaurants were so long, we went to McDonalds. We refuse to wait an hour to get into a restaurant when it's already 8pm, which is way past our dinner time as it is.
Berghoff's In the State Street shopping area, on Adams Street. We just stopped here to get a cup of soup for a midafternoon snack, but it was quite a nice place. The service was good, and so was the soup. The menu had a lot of interesting stuff-lots of German influenced foods. Casual atmosphere.
Buckingham's In the Chicago Hilton and Towers. A nice restaurant, but the service was way too slow. There were very few people in the restaurant, and yet it took an eternity to get our food. The crabcakes as an appetizer could almost be a meal-they were pretty good, too. The food overall was good, but not worth the wait.
Frango Cafe In Marshall Field's. A cafe not at all impressive especially when compared to the Walnut Room. The service was too slow, and the food was just o.k. You're better off going to the Walnut Room. (See below for review.)
Ghirardelli Soda Fountain On Michigan Avenue. All they serve here is ice cream. But they make the best sundaes in the world, bar none. Both the ice cream and the hot fudge are made with scrumptious Ghirardelli chocolate, which in the chocolate world is just a step below Godiva (and much more affordable). Do yourself a favor and stop in. You'll love it.
Kitty O'Shea's In the Chicago Hilton and Towers. An Irish pub-the seating here is self service, and a waitress will come around to you sooner or later. The food is very good, especially the corned beef and cabbage. Keep in mind there is no nonsmoking section, so if that bothers you, you might want to skip it.
The Pavilion In the Chicago Hilton and Towers. A very good breakfast buffet is served here. It's a bit pricey, but there is a nice selection, and the omelet station (they make them right in front of you) will appeal to some. They also have lunch and dinner buffets. There is a menu, too if you don't want the buffets, but once you price out what you're ordering you'll realize you should have done the buffet, since it's all you can eat. The service isn't that great, but it doesn't matter if you're doing buffet. When I wanted more orange juice and the waiter wasn't around, I just went to where they keep it and got it myself.
Walnut Room In Marshall Field's. A great place to eat while you shop 'til you drop at the best department store anywhere. The food is fantastic-the salads are huge and very tasty, especially the steak that was cooked to perfection that topped one of our salads, and the desserts are scrumptious. A must try is the Frango mint ice cream cake. The service is top notch. The dark paneled room and the fountain at the entrance lend class to this upscale, but casual restaurant. Don't miss it.
Where to Shop
Carson Pirrie ScottThe Disney Store On Michigan Avenue. Yeah, we know they're everywhere, but if you want a nice Chicago souvenir t-shirt or sweatshirt, they've got some neat designs here.
Marshall Field's The coolest place to shop. A huge department store, it's better than the New York City Macy's by a mile. It's beautifully built, and kept up nicely. Don't miss the Tiffany domed ceiling. You could literally spend days here shopping your heart out. If you're visiting from out of town, be sure to go up to the visitor's center and ask for your discount coupon book. If you're an out of towner, you get 10% off all your purchases (non sale stuff), as well as a coupon for a free cup of coffee, and a slice of yummy Frango cheesecake with purchase of an entree in one of the restaurants.
Neiman Marcus Michigan Avenue. Overrated and strictly for those who like to blow wads of money. If you can find anything that costs less than $50, we'd be surprised. And most of it is either way too outlandish, or else just not worth it.
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