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October 19, 2009


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It sounds like your lodging may be paid for if this is business travel, so this may be off-topic...but here's some info on how I save a significant amount on hotels.

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%.

We saved a TON of money with a local museum pass. We purchased a year long pass to the local Science Museum (I live in Fort Wayne, IN). Our museum offers discounts to lots of other museums, we spent a week there with three children and we saved as much as we spent on the family pass, plus we got to visit the hometown museum for the rest of the year.

Members of the Association of Science-Technology Centers Incorporated. Members receive free admission or discounts to 200 participating museums, including the Chicago Field Museum and the Museum of Science and Industry. Sometimes we got into the museum with a discount, other times we got to attend special exhibits for reduced or free. I've provided the URL to the website.

ALSO - check out the department of transportation website for Chicago. The Yes, you can take a taxi and boy will you pay out the nose for it. The CDOT has a page for visitors and transportation around the city.

If you are going to the John Hancock building you can safely skip the Sears tower. The views are both wonderful and the latter doesn't add much to the experience of the former. The lines and cost of the Sears tower are much greater.

I just came back from Chicago a couple weeks ago. I'm not sure how many activities you are planning on doing or how long you're staying, but I got my moneys worth by buying a Go Chicago Card. It let's you into over 30 places (as long as you're there before 5pm for most attractions). This way you still have the evening to do non-tourist things without wasting your time on your card. You can also go to the same attractions multiple times (just not on the same day).

I agree with Duane, you don't need to visit both the Hancock Tower and Sears (Willis) Tower. You get great views from both, just from opposite ends of the city. I think the Hancock Tower had a better view of the two, plus we didn't waste as much time in line.

I also purchased a CTA (transit) pass to use while I was down there. The public transit system is pretty good and way cheaper than taking cabs everywhere.

If you can, I'd also try to take the architectural boat tour from Navy Pier. It was one of my favourite parts of my trip!

Have fun!

I know it won't save MUCH money, but last time I was in Chicago some of those places offered a AAA discount. Hope that helps a little and enjoy your trip!

If you know a Chicago resident with a library pass you can get free tickets to all the museums. Every library in town has a certain number of free passes, and each pass will get four people into any one museum for free. The library will only let you check out one pass at a time, but at the prices the museums charge, even one pass is worth a significant savings.

Another way to save money is by patronizing the bar in the Hancock Tower. Rather than paying the fee to head up to the viewing tower (which I think is 15.00), just head to the bar/restaurant and order any drink (most less than 10.00). This way you can avoid the throngs of people on the viewing level AND enjoy a nice beverage while you look out at the skyline. As an aside: Make sure the weather is complimentary to viewing at all. Both the Hancock and Sears tower don't seem to have a problem charging people to view even on overcast days where all you'll see is a wash of cloud cover.

Enjoy Chicago!!

I live in a Chicago suburb. The ideas listed above are good. Discounts for many of these activities can be found on the following sites:

It is truly a great city. Good luck and Have fun!!!

Depending on when your going, I know the Entertainment books ( have a coupon for the Museum of Science and Industry. I have a coupon that expires at the end of the month if your going before then.

I highly recommend the Art Museum.

The Bean in Millenium Park is free.

The Chicago Tourism board is on Twitter at @explorechicago. They list free museum days and sometimes other specials.

Great suggestion above re: using Priceline for hotels. We did that two years ago during this same time of year and got a great hotel located next door to Hancock Center and Water Tower Place for only $50 a night.

If you're prepared to spend $20 or more a day to park. We went to the visitor center at the old water tower and got a discounted transit pass for everyone...that way we could leave the car parked at the hotel and then ride the buses and trains.

We were there to celebrate a child's birthday, so we were sure to mention that fact at every restaurant we went too. He got free cake three times! And at Portillo's (famous for Chicago hotdogs), they even made up a special song for him.

I wonder if your new Henry Ford/Greenfield Village pass is good at the Museum of Science & Industry?

All the above ideas are great. Sears tower has the new glass windows where you can walk 3 feet out and look down, so it might be more fun even if it is more expensive. All of Millennium park is beautiful and free and the lakefront is close by. Also, Lincoln Park, the Lincoln Park conservatory and zoo are free. The nature museum and history museum in Lincoln Park are considerable cheaper than other museums. You can often find free parking in Lincoln Park on weekdays. Downtown you will pay a lot for your meals and parking and need to factor that into your costs.

What about City Pass?

The Field Museum may not be on your list but it is fantastic, and then with City Pass you'll get your choice of Sears Tower or Hancock (I prefer Hancock; it's got a better exhibit about the city. But I haven't been to Sears since they added the see-through deck.) The Adler Planetarium is good, too. The Art Institute isn't included in City Pass, but it's also well worth visiting.

Whichever skyscraper you visit, I recommend going about 30 minutes before sunset. (Visit for exact times.) You'll have enough time to see the city, and then you can watch the sunset from a unique vantage point, plus you can watch the city lights come up.

Definitely use transit wherever possible, it will be so much easier if you're willing to spend a bit more time:

Both the Shedd Aquarium and Museum of Science offers many upcoming free days check them out here:

Most of the museums in Chicago have some type of free day attraction.
One way to save money on the Hancock Tower: Rather than buying a ticket to the observation deck, go on a weekday at lunch time to the 95th floor Restaurant. They have a good buffet and lunch menu. You don't pay to take the elevator up, so all you're paying for is your meal and getting the same view. Also there is a bar on the 96th floor where you can do the same thing and have a drink. The drinks aren't cheap, but it is much cheaper than buying tickets to the Observation Deck.

Visit the "Bean" at Millenium park! Free, and what dazzling perspectives!

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