Tips for a Chicago Vacation

Updated on March 16, 2008
M.R. asks from Saint Louis, MO
15 answers

My family and I are going to downtown Chicago for 2-3 nights in early June. We are planning to visit Shedd Aquarium, Michigan Ave., the beach, a fossil museum (Field Museum?), Navy Pier, and possibly the Hershey's shop and Sears Tower.
Any other suggestions/advice would be appreciated including helpful websites for navigating the streets or riding The El. BTW, it's just my husband, me, and our 9 y.o. daughter.
UPDATE: based on the responses, we are leaning toward taking a bus or train to chicago and leaving the car at home. We've found so much to do that we will stay 3 nights now. I hope we can get it all in. i wish we could stay longer! I may be a Cards fan/Cubs hater ;) but I really like Chicago. I've been there once and loved it. We will have so much fun.

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So What Happened?

Wow! So many great suggestions! thanks so much for the tips. i will definitely check out the Rainforest Cafe. The more i hear, the more i think i'll just use public transportation. thanks again!

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answers from Peoria on

Try to use the public transportation as much as have to pay to park everywhere....and it is very expensive.....Even have to pay to park in the mcdonalds parking lot to eat at mcdonalds. There is a really neat looking place to eat downtown....It is called the Rainforest Cafe....I dont know if there is a website or not but you can try looking. Have a Great Trip.

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answers from Rockford on

Wow! That about covers everything I could have suggested, lol! Here is a site that has maps, restaurants, activities, museums, and more. I hope I could help!

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answers from Columbia on

If you're driving to Chicago, you'll obviously have your own car. But if you're flying, it might be cheaper to take a taxi. Parking in Chicago is extremely expensive. Just at the hotel (if it's downtown) is at least $24-$40 a day. Then if you drive, you deal with directions, traffice, arrogant taxis, and parking again.

As for hotels, I don't recommend Congress hotel on Michigan Ave. For some reasons, it's advertised everywhere but people don't realize they're overpaying. I would recommend It allows you to bid for a cheap hotel. I always go in and bid for a 4 star for around $60-$70 a night. You might have to try several times and there might not be many cheap rooms since it is summer.

I recommend the boat tours! You take a boat for 1 hr-1.5 hours and tour Chicago on it. Very fun. It can be as cheap as $20 a person or as expensive as $30?

Don't go to the museum with a 9 year old unless they're really interested. Museums are boring for children unless they're naturally interested in them.

Hancock Tower is another popular choice. Below the tower, there's a famous Cheesecake Factory that many tourists eat at.

Shopping (even window) is great on North Michigan Ave. Some stores are out of my leauge and high-end but it's fun to walk around.

Millenium Park is right in the middle of Michigan Ave.

Art Institute of Chicago Art Museum is my personal favorite place. It's locate near Millenium Park as well.

For restaraunts, I would recommend Giordano's and Bennigan's. Giordano's is famous for deep dish Chicago pizza. Bennigan's is a classis choice but unofrtunately, we only have 1 in Missouri. I recommend the Monte Christo at Bennigan's.

Have fun!

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answers from Springfield on

We purchased the City Pass. It saved us a bunch of money. We went to the City of Chicago web site. If you are taking your own vehicle, park under the soccer/football field by Shedd Aquarium. Park before 9:00 a.m. and it is cheaper. It does fill up very fast. We park all day under the field. Other parking places are very expensive. We spent $25.00 for parking by the John Hancock building. We could not find parking for the L train so we were not able to save on parking.

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answers from Bloomington on

We travelled to Chicago for Spring Break. I suggest going on line and purchasing your tickets for the museums and the Aquarium before you leave. The lines for tickets are extremely long and if you already have your tickets you will avoid lines and be able to enter quickly. Saves lots of headaches and cranky kids too.

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answers from Springfield on

Oh that sounds like fun. We've done the chicago weekend a couple of times. My tips are:

Visit the aquarium first, then walk to the museum and get there when they open! It's much nicer to beat the crowd.

Depending on where your hotel is there's a free trolley to Navy Pier, we took that when we stayed at the Mariott Downtown.

Some things to not miss:
-The Rainforest Cafe - your daughter and you will love it! It's a tad pricy but such an awesome experience and food. They have a website I believe.

-Try different places for deep dish pizza. We went to Gino's and another one with a G name, but I can't remember it. They both had some awesome, seriously deep pizza.

Hope you have a great time!

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answers from Peoria on

Another place to check out is a theater group called Barrel of Monkeys. They take childrens stories and peoms and turn them into very funny acts. People of all ages, including kids, love it.

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answers from Peoria on

I know you have received many suggestions, but I do have a few more.

First, for ice cream, a very old town, famous ice cream place is tiny and cramped, but the most amazing place. It is called Margie's and it is at the intersection of Milwaukee Ave, Western Ave and Armitage Ave (a six corner intersection). It has the best ice cream, home made fudge sauce, and old fashioned decor. Not an experience to be missed.

Margie's Candies

1960 N Western Ave
Chicago, IL 60647

Also, a more relaxing way to spend an afternoon is down at the beach, which can be walked to from Lincoln Park Zoo. My 8 and 10 year old girls love to just wander the beach collecting things, but swimsuits are even better. What a way to unwind, instead of racing around the entire trip.

Also, they rent multiple person bicycles on the riverfront and I am sure you could get one for the three of you.

I hope you enjoy your vacation! I lived there for 12 years of my adult life, moved back to my hometown of Peoria a couple years ago and really miss Chicago. It is a wonderful place to be!

I agree about the museums and your nine year old. She will enjoy the children's museum on navy pier probably much more than the others. It has mostly interactive exhibits. My kids love it there. It is also a great place to catch a boat ride, and there is the huge ferris wheel. Many shops, including Haagan Daaz, yummm.

Also watch for the free trolly's that go between some of the attractions.



answers from Bloomington on


Don't forget the Lincoln Park Zoo. It's Free!!!! It would easier to just take taxis around town. If you drive your own car you will have to pay for parking. Have fun




answers from St. Louis on

I lived in Chicago and have relatives there. Although the Sears Tower is the tallest, consider going to the John Hancock at NIGHT. It is the most amazing view of Chicago. Go to the lounge/restaurant at the top. It is VERY pricey but just order drinks at the lounge, or ask to use the bathroom and then make an excuse to leave. The skyline at night is breathtaking. The J. Hancock building is right next to the Water Tower Place high rise mall. The door to the JH restaurants and lounges is on the S SIDE of the building. Make sure you use that entrances and ask somebody if you aren't sure. You might also want to book a tea lunch at the American Girl store/museum. It is really cool for girls. Husbands and grandpa do go, but it is a girly thing. But you can send you hubby to the NIKE store on Michigan Ave while you do the girl thing. Have fun and bring a lot of layers and sweaters, as it is always colder than you plan.



answers from St. Louis on

Go to the American Dolls Store. It is Amazing!! I do not know if your daughter would be interested or if she is to old but it is sooooo cool!!!!



answers from St. Louis on

I would recommend a stop at the Chicago Cultural Center when you arrive:

It borders Michigan Ave. on the east, and takes up the block between Randolph on the north and Washington on the south. There is a visitor's center inside that can give you any information you need about getting around the city (public transportation is GREAT) as well as what to see. You can get City Passes there which have admission to popular sites like the aquarium - the passes also tell you what are the free-admission days, which are the days to avoid as the sites will be very crowded (field trips, etc.).

If you don't plan to see all or most of the sites offered in the Passes, then you can get plenty of other information at the cultural center. I don't believe you can go to the top of the Sears Tower any more (since 9/11), but you can go to the top of the Hancock building.

I'm not sure if you've been to Chicago before or not, but it's a wonderful city with a LOT to see and do - and don't be surprised if you leave your car in the parking garage your entire stay. Also, there is an architectural boat tour that lasts about an hour or so that takes you through downtown and highlights some amazing buildings. Your 9yo may or may not enjoy that.

Sorry to ramble - have a great time!



answers from Springfield on

We go to Chicago every year as a family. Everyone has mentioned lots of good ideas. Lincoln Park Zoo is just a little north of Water Tower, but it's neat and FREE. You can get there by bus. Get visitors passes online at the CTA website. They are much cheaper than regular passes, and good for the bus and the el. Have you seen the broadway show "Wicked"? The book is raunchy, but the show is wonderful. There is just one song that is a love song and they kiss at the end, but it is perfectly fine for a nine year old. We've seen it twice. You can get tickets at Broadway in You could check out the Children's Museum at Navy Pier. Your 9 yr old will still enjoy it. There is a Cheesecake Factory restaurant at the bottom of the Hancock building - fabulous! Also, across from the Hershey store is a Ghiradelli Ice Cream Shop. Even if you don't get ice cream, when you walk in, they give you a free chocolate.



answers from Detroit on

Sounds like you have a lot planned! You can always visit buckingham fountain--it's just a big fountain, but it's a very beautiful area of the city. Also, any of the museums in downtown Chicago are great for kids--I like the field museum best myself, I have such fond memories of it from growing up, they have a giant pyramid you go through to learn about ancient egypt and a ton of other great exhibits, I'm not sure what there rotating exhibit is this year...but I'm sure you could find it on their website. Also, if your daughter is interested there is a huge American Girl store--that's always a big hit, as well as going through the huge FAO toy store on Michigan Ave.

Also, it's great you will have a car for some of the far away type trips you may make, but I would suggest using public transportation as much as possible. It's easy to use and a lot cheaper--in fact, you could think about getting a 3 day pass and you can use CTA as much as you want for a set price...I only say this b/c parking will be around $15 each time you re-park. If you want to get a feel for routes you would take from your hotel using CTA you can go to their website (I'm not sure what it is, but it's probably or google Chicago Transit Authority), they have a feature that allows you to put in different stops and it suggests how you take it. The EL is similar to the metro here in st. louis and is very convenient and easy with trains running every few minutes for each line--the longest I've ever waited has been 10 min and that's when I just missed a train.

Hope you have a great time! If you need any more help, please feel free to send me a message, I grew up in the Chicago area and just recently moved to St. Louis.

~R. K.



answers from St. Louis on


I was in downtown Chicago in November of last year for the Oprah show. Shedd Aquarium is the neatest aquarium I've been to in a long time, and I've been to tons!! Your daughter might enjoy the American Girl Factory, I believe they do daily tours. Also with driving your own car I have to say it will cost you an absolute fortune in parking, be preparred to pay a good 20$ to park just about anywhere. We had our car and after paying for parking a couple of times we decided it was cheaper to split a cab. Don't forget to have pizza, it's so good and also there is a cereal bar, yes cereal. You can bring your daughter and I'm sure she'd like it and what an experience just to say you've been to a cereal bar!! Have a blast.

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