Free Ebook.

Enter your email address:

Delivered by FeedBurner

« Help a Reader: Variable Annuity | Main | You Don't Have to Save Every Penny »

April 14, 2009


Feed You can follow this conversation by subscribing to the comment feed for this post.

There are so many things to do in Chicago, but if I had to name my top favorite, it would be taking the Chicago River cruise. One of the stopping points is Navy Pier (where you planned on going).

One of the mot beautiful places I've ever been is Niagra on the Lake. Not far from the main attractions. I have family in the area and have been there dozens of times. The main area in the downtown -very touristy-is Lundy's Lane. You'll find rides, wax museum, food, hotels, etc. The botanical gardens are very nice and well worth seeing. The falls have free walking area with spectacular views. The boat ride "maid of the mist" is an interesting but expensive outing.
My best advise is
1. AAA guidebook for the area. The front of the book shows all the attractions and what the hours and costs are. We use these on every trip. Helps with planning and budget.
2. All the attractions can be walking distance if you stay in the downtown area. Find the best hotel at the best price (again using AAA guide an online site such as expedia).
3. Check out the offical Niagra Falls visitors site.
They will show all the special events and the nightly fireworks and lighting schedule. This is a really nice show. It will also have specials and packages that are sponsored by the tourist board.
Most of all have fun - this sounds like a great vacation

Correction to above post- start of tourist area is Bridge Street, Lundy's Lane is hotels, shopping and food.

I second Niagara on the Lake! Very neat.

I've worked on the American side of Niagara Falls for 9 summers. The main thing that I know is that the American side is the more "nature" side, whereas the Canadian side is more "tourist". I'd suggest spending a bit of time on each: walk around Goat Island (the American side state park), go on the Cave of the Winds and the Maid of the Mist, get the trolley tour. Then, for the activities, go to Canada's boardwalk and play mini-golf, see the museums and haunted houses, ride the observation tower, etc.

If you want a nice view for dinner, I'd recommend Top of the Falls restaurant, on Goat Island - it's a bit pricey, but less so than the snack bars and vending stands around the park (which I supervised for half my time). Amazing view of the Falls, and a great atmosphere.

If you need any other suggestions, let me know - I'd be glad to help.

I'm going to assume that you're relatively new to Chicago. I've been there several times and Chicago is a pretty cheap city to travel if you do so between Memorial Day and Labor Day. They have a free trolley service that runs from Union Station to pretty much anywhere that tourists want to go.

For something totally free you can tour Millennium Park and see the Bean, the concert hall (you may randomly arrive in the middle of a free concert) and the other attractions there. Not much to actually do but it's all stuff that should be seen.

You should also go to the top of the Sears Tower (soon to be rechristened as the Willis Building). It's a rip off but it's probably something that your kids will enjoy. I loved it and I'm in my 30s.

As for museums, the Science and Industry Museum, the Art Institute, the Shedd Aquarium and the Natural History Museum are must sees. I would check the websites before you go to see which big exhibits are showing. That might help you prioritize. I don't think too highly of the Planetarium as it really needs to be revamped. Also keep in mind that any of these museums can easily be an all day event.

When you get to Navy Peer consider taking a boat tour. There are two options given by a couple of different companies. The first is a skyline tour where you boat out into lake Michigan to get the best possible view of the Chicago skyline. Bring your cameras. The second is a boat tour down the Chicago river that also includes a lecture on all the major buildings. Architecture, engineering and political wheeling and dealing are all discussed.

If you go to Navy Peer bring water bottles. The price of water is insane and you WILL get thirsty. Your kids will probably love the giant Ferris wheel.

Chicago has other tours available including walking/trolley tours and segway tours.

If you are willing to venture into the suburbs a bit check out Oak Park. Frank Lloyd Wright's studio is there as are several houses that he designed.

Chicago has two zoos (Lincoln Park and Brookfield). A combination of the Metra and taxis can get you to either one on the cheap.

And that's enough to easily keep you busy for a week. As for shopping, I'm not a shopper so I'll leave that to people more knowledgeable than I.

I've always enjoyed going to Ed Debevic's on Wells St. to eat whenever I'm in Chicago. It's been a few years, but I'm sure it's still fun. I'll second the Sears Tower, overpriced, but still a sight to see.

Have fun!

Stupidly Yours,


I would definitely suggest the Shedd Aquarium. My husband and I went there right before we got engaged and I thought it was amazing. You might look into ordering tickets ahead of time because the line can get long. Michigan Ave. is famous for its shopping and we have spent a lot of time just walking up and down checking out different stores. I would have to say that my favorite city in the U.S. is Chicago so I am jealous of your planned vacation there! :)

The Lincoln Park Zoo is free, at least it was the last time I was there. If your kids are young they will like it. There are better zoos, but it's worth seeing....since it's free.

The Shedd is pricey, but if you join, or are already a member of the national association the Shedd is affiliated with, you get in free. Go to their website for details.

We stopped in Niagra on the way from Parry Sound two summers ago. We took the Maid of the Mist tour for $50 Canadian (family of 4) and found it worth while. Otherwise, I would get out of Niagra as quickly as possible. It's a very expensive tourist trap. But the falls are worth seeing.

In chicago don't take a cab unless you have to, take the L...

At the niagara falls, i didn't think any of the things in the area were really worth doing.... There is a much better view from the canadian side, but honestly, I would bet staying on the american side would be way cheaper.... just something to consider...

Check yelp regarding reviews of things before you do them... Though behind the falls might be cool, it wasn't open when I went (in February)... My website is my yelp page, check out the things in the Niagara area

I've lived in Chicago all my life - if you have questions or are unsure of anything feel free to send me an email, I'd be happy to help.

Also, check out your local bank website... I know bank of america offers free admission to some museums in boston (if you show your BoA card)

I live in Chicago. I would recommend the Shedd over any other museum we have. I think the free trolley service was discontinued this year due to the economy so don't count on using that to get around. The Sears is cool, but pricey. I think you can go up to the Signature Room at the Hancock and have a drink so you get the view without paying for tickets. Take the red line up to the Addison stop and see Wrigley Field. Not sure if there will be a game going on the weekend you come, but if not you can take a tour of Wrigley Field for a small price. It is quite interesting and you can get tickets in advance on-line. Definitely walk around Millenium Park. Ed Debevic's is a tourist trap that has nothing to do with Chicago. If you don't mind a wait go to the original Uno's or better yet check out one of the many great local non-chain restaurants. The architectural cruises are definitely worth it. Wendella boats leave from the Wrigley Building on Michigan avenue. I think they have a combo river/lake cruise that gets you a little bit of the traditional river architecture cruise with a chance to go through the lock out into the lake to see the sky line. Try to time it around sunset if you can.

This website offers a list of dates that the museums are free in Chicago.
The Museum of Science and Industry was always my favorite as a kid. I agree with the previous reader that Ed Debevic's is a tourist trap and rather expensive, and also that you can get a great view from the Hancock with out the price of Sears Tower.

We live 40 miles west of the downtown Chicago and we enjoy biking the lake front trail and eating at some of the great places downtown. The trail goes at least as far south as the Museum of Science and Industry and nearly as far north as Evenston (Not exactly sure). We make a day of it and enjoy the beaches, sites, and food, not to mention the exercise. My parents have been biking the lakefront for almost 50 yrs and they took us as soon as we were old enough. Pizzeria Uno/Pizzeria Due has great deep dish pizza. Due's has more seating and might not be too crowded before 5pm. It's just a block down from Uno's. Let me know if you have any questions, we'd be glad to help. Thanks for the great blog.

Regarding Chicago, I agree that the Shedd is a great spot. But keep in mind that the oceanarium is closed until May 22nd.

I'd also recommend the Hancock over the Sears Tower.

The architectural cruises are not cheap, but definitely a great way to see the city and spend some time.

Buckingham Fountain is in the process of being fully restored. They have just finished the first half and, seeing it at night Sunday night, it would be a fun thing to see with kids.

You should also check out the calendar of events. You could time your trip to coincide (or not, depending on your interest) with one of the many festivals that happen in Chicago.

If you like botanical gardens or conservatories and are willing to venture out a bit, the Garfield near Washington Park is nice and so is the Botanical Gardens up in Highland Park. Another idea would be to catch a concert with the family at Ravinia. It should be in full swing come June and lawn seats usually are only ten bucks a person. You can take the train right to the concert park from downtown for 5 bucks a person.

Why am I moving from this city?! Oh yeah, liking being employed versus unemployed...

Wow, you have a lot of comments already! I didn't get a chance to read all of them, so sorry if I duplicate some things here.
One of my favorite travel sites is (no, I don't work for them / get a kick-back of any sort!). They do a really good job of compiling user reviews as well as providing a way for you to purchase reservations, compare prices, etc. You may want to see what they have to say.
We just visited Niagara Falls last year. The views are spectacular from both sides. The U.S. side is a bit less touristy. We were childless travelers at the time, so had not use for Clifton Hill (on the Canadian side), but you may want to look into it if you have kids. Also, we enjoyed the Maid of the Mist... a bit pricey, but worth the money IMHO.
Enjoy your trip!

I was in Chicago last September and there were a lot of panhandlers, seemingly more than we have in Houston. Only mentioning it, because you might want to address the subject with your children beforehand, or at least think of what your response will be, if they've never been to a big city and seen that. I know my daughters first encounter with a panhandler was confusing for her, and caught me offguard as to what I should tell her. Other than that, the city is awesome, even better than Houston as far as atmosphere and architecture. Enjoy!

I also live in Chicago, and I know from hosting visitors that it's easy to spend a lot of money as a tourist and not really see the city.

My advice:

1- Don't stay right downtown. Find an Inn or B&B in one of the neighborhoods (Lincoln Park, Lakeview, Lincoln Square, Bucktown, Wicker Park) — it will be much cheaper and you'll get a more authentic experience.

2- There are some great museums, but they are expensive and very time-consuming if you want to get your money's worth. I'd say, pick one museum and spend to spend a full half-day there. If you do multiple museums, you'll see a lot of great stuff, but you won't really see Chicago.

3- Avoid Navy Pier at all costs. It's a tourist trap.

4- Use Yelp to find restaurants in Chicago. Yelp's reviews and data on Chicago restaurants are top-notch and I use them all the time (even though I live here).

5- Take the L! It's pretty easy to figure out and the older, above-ground lines downtown are a lot of fun.

Oh, and enjoy your trip!

I would second Niagara-on-the-Lake. My wife and I love it there. If you are spending more than one day in the area you may want to look into the Jet Boat tours (, though more suited for older children. I haven't been on it but I have seen it and it looks like a blast, and everyone I've talked to has said it was a lot of fun, though very pricey. There are also plenty of wineries in the area. Clifton Hill is a big tourist trap, though the kids may get a kick out of it. We enjoyed the White Water Walk, which is down the river a couple of miles from the falls where you take an elevator to the bottom of the gorge and walk along the river rapids.

For Chicago, if you will be using public transportation, check out the CTA website. They have really helpful trip planning tools. You can also pre-order three day (I think) passes for somewhere around $12 for unlimited L/bus transport.

If you will be hitting a bunch of museums and there are specific exhibits you want to see, I'd also suggest ordering tickets ahead of time. The Museum of Science and Industry gets pretty busy on weekends. Another option is CityPass, which can be a good deal if you'll be doing a bunch of attractions. It's a package deal for admission to five sites around the city.

I second the above recommendation of TripAdvisor. The restaurant and hotel reviews are really helpful!

Several others have already mentioned the Museum of Science and Industry. There are countless fascinating things to see there, for all ages. Here is a link to see some of their exhibits:

Some years ago, I read a book about Colleen Moore's Fairy Castle, which was donated to the museum. The pictures and descriptions were so impressive that it made me want to drive the 600 miles or so to see it.

Fate stepped in, and my company sent me to the Chicago area for 2 weeks of classes. On the weekend, we visited several places, including The Museum of Science and Industry.

Just thinking about it makes me want to see it all again!

Thanks for your comments, everyone. You've been VERY helpful.

Niagara Falls - I HIGHLY recommend either Cave of the Winds, Maid of the Mist, or both. The falls are pretty when you just stand there and look at them, but both of these attractions get you as close as is safely possible, and you really feel the power of the water.

We are taking a family trip there this summer, as well (along with my in-laws, who have never been). My big concern now is what is good to do with a baby along.

Chicago - I have visited my wife's relatives who live out by O'Hare airport. I have found some of the best hotel rooms - size, price and features (pools, in-hotel restaurants, etc...) there. Use hotwire - 4 stars and up. The drive into the city isn't great, but if you go at off-hours, you'll do fine. I've also heard mass transit can get you downtown easily. I enjoy the ethnic neighborhoods around the city, and you can find some great new foods from Food Channel celebs like Rachel Ray and Guy Fieri (search "40 dollars a day" and "diners, drive-ins, and dives"). Parking downtown is awful; the zoo is great.

Thanks for your blog - I've been encouraged and challenged by it over the years.

I know I'm late to your post, but I just noticed your travel plans post referenced in your "what I'm doing now" post.

I haven't seen you discuss this before, but it may be worthy of a stand-alone discussion.

If you are traveling to a big city...NYC, Chicago, LA, Miami, etc. you can save significant $'s (often 50%) by bidding on Priceline or by buying an opaque listing on Hotwire. You have to do your research and understand the risks (you can't bid for a specific hotel) in order to ensure a pleasant experience. There are two websites where people post their Priceline wins...which gives a bidder an idea of how much to bid and which hotels you might have a chance to win. The websites are (Priceline and Hotwire info) and (Priceline info). Please use their links to support the sites so that we can continue to have these great resources.

There is a specific strategy using "free rebid" zones (you add the zone to bid again, even though it doesn't have any hotels with that star rating, so you don't have a chance of winning that zone) that allows you to bid many times to ensure you get the lowest possible winning price. The more advanced bidding is called permutation bidding, where for example you can have 31 free rebids (chances to guess the lowest price that will be accepted) if there are 5 free rebid zones in the city. Here's a link to the premutation bidding (
It's not that hard, but it does take some planning and practice. You have to seet up a plan before you start bidding and then stick to the plan even if you don't win that day.

Last year, I was able to get a great hotel in Chicago (the InterContinental) in the middle of that silly Lalapalooza for a great price. The year before, I won the Omni in the financial district of San Francisco for a price that was about 50% off and it turned out to be another great hotel. I typically only bid for 3 or 3 1/2 stars or higher as both Priceline and Hotwire sometimes inflate the star ratings.

I have also used Priceline to win car rentals at a decent discount 30%.

The comments to this entry are closed.

Start a Blog


  • Any information shared on Free Money Finance does not constitute financial advice. The Website is intended to provide general information only and does not attempt to give you advice that relates to your specific circumstances. You are advised to discuss your specific requirements with an independent financial adviser. Per FTC guidelines, this website may be compensated by companies mentioned through advertising, affiliate programs or otherwise. All posts are © 2005-2012, Free Money Finance.