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Chicago took me totally by surprise. I didn't expect to like it. Not only did I like it, I loved it. We flew into Midway and I was amazed at how easy and inexpensive it was to get from the airport to our Bed and Breakfast. Yes we stayed at a downtown B&B, Flemish House off of North Michigan Ave and it was amazing. The location is fabulous and the hosts very welcoming. You don't get a cooked breakfast but you get what you need in your apartment everyday to make you own breakfast. Without doubt our bed there was the most comfortable that I have ever slept in and all at a very reasonable price.
1. Use the Chicago transit authority's web site www.transitchicago.com to plan your trip. You can put in the address where you will start your trip and where you will end it and the site will tell you exactly how to get there. It even lets you put in the time of your trip and it will tell you how long you should have to wait for your next connection. Purchase a day pass, 1, 2 or 3 days. If you are going to be in town more than 3 day buy the 7 day pass it will be the better buy. The day pass is good on the L and on the bus and can also be used to get in from Midway airport. We bought ours at the Station at Midway.
2. Take one of the Trolley Tours. It is amazing how much this helps you to get your bearings. We took a hop on, hop off tour; there are several companies that offer these. We went through almost all the way then got off at the Art Institute. It helps if you have an early start to your day this way you can go all the way through one time and then get off at the places where you would like to spend more time.
3. Take an architectural river cruise. You will see Chicago from a perspective that you won't get from anywhere else. The range and scoop of the buildings is amazing and the river itself has a story to be told.
4. Walk up Michigan Avenue and enjoy window shopping, you will find all the major designers represented here. While you are there stop at the Visitor Center and get all the local information that you will need for a great visit. For anyone with young daughters, nieces or granddaughters the American Girl Store is a must.
5. Walk on Navy Pier. From here you can take a cruise of Lake Michigan, visit the Stained Glass museum (free) take a Ferris wheel ride, watch a play at the Shakespeare Theater or just go and have lunch or dinner at one of the many restaurants. We also enjoyed the displays along the pier of the vehicles that have been pulled out of Lake Michigan.
6. Rent a bike and pedal your way around some of Chicago's ethnically diverse neighborhoods.
7. Go to the top of the country's tallest building the Sears Tower. The views from the observation deck are amazing.
8. If you can only do one museum make it the Chicago Institute of Art. This is a world class museum that really is in a class by itself. A very deep collection of old masters, American artist and impressionist and post impressionists.
9. Get tickets to one of the shows, Broadway or comedy take your pick both can be found in abundance. I am going to suggest that you buy them as far in advance as you can since they are very popular.
10. Be prepared for the wind, it isn't called the windy city for nothing.
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Chicago: Travel tips for the Windy City
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