We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.


Free Newsletter

Interested in Chicago?

We'll send you updates with the latest deals, reviews and articles for Chicago each week.

More Lists
Lists you may be interested in:
Trip List by moseylou

Chicago for the first time

8 Aug 2006  fun trip to Wrigley to see the Cubs, and so much more!
3.5 of 5 bubbles based on 3 votes

recommendations for those traveling to Chicago for the first time

  • Explore locations featured in this Trip List: Chicago
  • Category: Recent trip
  • Traveler type: Sightseeing, Never been before
  • Appeals to: Couples/romantics, Singles, Families with small children, Families with teenagers, Students, Budget travellers , Active/adventure, Tourists
  • Seasons: Summer
  • 1. Chicago Double Decker Tour bus

    take the chicago double decker tour bus, not the grey line one the other, the first morning of your visit. We do this in every city if they have one. It's a great intro to the city, and you can jot down places that intrigued you to return. You also get an idea of the "scale" of the city in terms of how far apart things are that you are interested in. The regular tour is 2 hours, or the hop on/hop off allows you to be spontaneous and get off at something that you want to visit. However, don't think that you'll use it in place of the public transportation system - the frequency is just too uncertain to depend on it for that.

  • 2. Chicago Public Transportation

    when you arrive at OHare or Midway, get a visitor pass for the CTA. The train and bus system is EXCELLENT, and really allows you to explore the city and get to a lot of places quickly in a city the size of Chicago. The neat thing about the visitor passes is that they activate when you first use them, not when you buy them. So, for example, if you were going to be using it a lot the first two days, and then not for the third day because you were doing something specific, and then you wanted one the last day for running around and getting to the airport, you could buy a two-day pass, and then a one-day pass that you didn't activate until that last day. Make sure you get a public transportation map (I got one at airport information) - it'll be raggedy and well used by the end of your trip!!!

  • 3. Goose Island Wrigleyville Brew Pub

    We really enjoyed this restaurant before and after the Cubs games. If you like microbrew, you'll like this. My husband is really picky about his beer, and he liked it. I really liked the wheat ale. The food was pretty good, and the service was great and fast when they knew we were going to the game and were running late. We even went back after the game for dinner!

  • 4. Millennium Park
    Millennium Park, Chicago, Illinois

    fabulous park in Chicago, near the Art Institute. If you've got little kids and visit in the summer, it's got a great splash fountain with these cool cascading fountains that have video of Chicago residents. There were a ton of kids splashing around in it the day I was there. The Pritzker Pavilion is absolutely gorgeous; I didn't get to attend a concert there, but apparently they have free concerts quite frequently. I would definitely take one in there. You can also rent bikes in the corner that's nearest to the Navy Pier, which my husband did and rode all up and down Lake Michigan for two hours. The Lurie Garden is small but beautiful as well, and I saw a great exhibition of panels about gardens around the world. I would love to see it at night - I would imagine it's beautiful all lit up. Oh! and I almost forgot! The "Cloud Gate" sculpture (or the "giant jellybean" as the kids refer to it) is really fascinating.