How to save big money during big-city trips

Recent visits to a couple of the nation’s most expensive places – New York City and Chicago – motivated me to figure out how to live it up while saving a few bucks. Among the strategies:

Buy an Entertainment coupon book for the metropolitan area that you plan to visit. These thick guides contain hundreds of discounts and typically cost $30 to $40 in November, but now that it’s June, pay just $12.99, plus $5 for shipping.

We ordered an Entertainment book for NYC and used the coupons to purchase at least $50 in meals and entertainment admissions. It helped us make decisions in a city filled with a paralyzing number of options. Had we decided to be aggressive about it, we could have doubled or tripled the savings during our three-night stay.

Two especially excellent finds: Jewel of India Restaurant, in the Theater District, and Caesars Italian and Continental Restaurant, just off Fifth Avenue at 34th Street. Great meals, pleasant surroundings, acceptable prices.

Upon our return to Wisconsin, I handed off the book to a friend, who has sons living in the Manhattan metro area.

Like the Entertainment books in Wisconsin (they exist for Appleton/Green Bay, Madison and Milwaukee), some places are out of business by the time the book is published. So call for a reservation before calling a cab.

For more:

I’ve yet to see “Wicked,” the hit musical about the Witches of Oz that has been in Chicago for one year, but it’s not for lack of trying. It’s for lack of luck, but yours could be different.

Tickets to the open-run production at Chicago’s Oriental Theatre typically need to be ordered months in advance and average $85 per seat. But on every show day, around 20 people get to see “Wicked” for just $25.

That’s because of a ticket drawing is held two hours before each performance begins. Just show up at the theater box office, 24 Randolph St. (or the Borders bookstore at 150 N. State St. on weekends), and enter. If your name is pulled, you can buy up to two tickets in the front two rows for the next show.

For more: Similar drawings take place for “The 25th Annual Putnam County Spelling Bee,” now showing at Drury Lane Theatre, 175 E. Chestnut St. For more:

When we came up empty-handed, a Hot Tix booth became our next stop. Theater ticket discounts typically are 25-50 percent, and that’s how we snagged entry to a funky Blue Man Group matinee. Good ticket choices exist; just be flexible and make sure the chosen theater is easily accessible.

My partner gets a little nervous whenever I go shopping on eBay, but I’ve never gotten burned. That’s how we obtained tickets to two hot shows on the East Coast: “Three Days of Rain” with Julia Roberts and the closing weekend of “The Odd Couple” with Nathan Lane and Matthew Broderick.

Start your ticket hunt early, and bid strategically, swooping in shortly (as in two or three minutes) before the online auction ends. We saved 20-25 percent off of the face value of what we won.

We ended up at the Guggenheim Museum on a rainy afternoon, and while waiting to pay our admission were reminded of CityPass, the one-price ticket to a half-dozen respectable attractions. The $63 NYC pass included the Guggenheim, American Museum of Natural History, Museum of Modern Art, Empire State Building Observatory, Intrepid Sea Air Space Museum and a sightseeing cruise.

In Chicago, its just under $50 for entry to the Hancock Observatory, Field Museum, Shedd Aquarium, Adler Planetarium and Museum of Science and Industry.

Savings total around 50 percent, assuming that you want to see everything covered by CityPass. Boston, Seattle, Hollywood, San Francisco, Philadelphia, Southern California and Toronto also have a version of this discount. For more:

Our overnight in Chicago was thanks to my need to use up Midwest Airlines frequent flier miles, or lose them. There weren’t enough to cash in for a flight but enough (15,000) to stay at the classy Swissotel, off Michigan Avenue.

Other options for attractive discounts, particularly in lodging:, an online and Wisconsin radio shopping show effort that results in savings of at least 50 percent. At this time of year, though, most hotel stays must occur on a weeknight for the discount to apply.

I always check the restrictions, and I tend to make the reservation before making the coupon purchase. That way, I know the property will be available on a date when I need it.

What else? Consider a bed and breakfast stay during your summer vacation. Members of the Wisconsin Bed and Breakfast Association are offering guests a $20 gas voucher with a Sunday through Thursday stay. For more:, and 715-539-9222.

If heading to Chicago, park in Kenosha or Harvard, Ill., and take the Metra train into the city. A Saturday-Sunday pass is merely $5, and it allows you to hop on and off as many times as you want. Also $5 is a one-day city transit pass, which allows unlimited rides on Chicago’s buses and elevated trains.

For more: and 312-322-6777; and 888-968-7282.