10 Best Ways to Spend $20 in Chicago

By Carrie Kirby on 28 May 2014 (Updated 8 September 2014) 1 comment

Despite its Midwestern location, Chicago is not a cheap city; a stroll down the Magnificent Mile will make that clear. Still, affordable outings can be had if you know where to look. Here are the 10 most fun, satisfying, or edifying adventures you can have in Chicago for about $20.

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And even after you and Andrew Jackson have parted ways, the fun won't be over, because you can still go see The Bean in Millennium Park — it's free. (See also: $20 in San Francisco: The Best Ways to Spend It)

1. Laugh Your Face Off

Chicago is justly famous for its sketch comedy troupes, crowned by The Second City. While Second City's main revue starts at $23, other hilarious acts at the famed theater go for $17 a ticket. Order on the phone and the service fee brings the tab to exactly $20, or walk up to the ticket office and save the extra $3 for a drink.

2. Cry Your Eyes Out

No ballpark in America is more guaranteed to make grown men (and women) cry than Wrigley Field. Whether it's the beauty of the Friendly Confines or the Cubs' heartbreaking knack for blowing leads, this place gets to all of us one way or another. You can spend well over $200 on a seat by the dugout, but you can easily get into the park for under $20. StubHub lists a number of Upper Deck seats for $18.50 or less, and the box office sells standing room only tickets on game day; at last check these were still well under $20 each.

3. Sink Your Teeth Into Meat

Sink your teeth into some encased meats, that is. Anyone can say they went to Chicago and ate a hot dog, but if you want a real Chicago hot dog experience, you have to line up at Hot Doug's Sausage Superstore and Encased Meat Emporium, where a new wild game sausage is featured each week, and where the dog formerly known as the Shawon Dunston is now called the George Mitterwald (it's a chicken sausage on a bun). Two hot dogs, two orders of duck fat fries, and two "pops" (sodas) will run you about $20. (But hurry! Hot Doug's will close for good in October 2014.)

4. Go for a Swim

A Western newspaper travel editor recently visited Chicago and expressed surprise that the city has beaches. Oh, yah! Chicago has 26 miles of lakefront, and on summer weekends, favorite beaches will be crowded from the North Side to the South Side.

City beaches don't charge entrance fees, but at some you'll need to pay for parking at meters or in pay lots.

If you score free parking, you can save your $20 for umbrella drinks at one of the beach bars.

5. Take a Walk

Walking tours with the Chicago Architectural Society run from $10-$31, and you can learn about the Chicago Board of Trade, famed architect Daniel Burnham, and many other topics. The Society's boat tours are more renowned, but the only way you can get one of those for $20 is to pair up with a member, who can get the $37.85 tickets two-for-one.

6. Ride a Ferris Wheel

The world's first Ferris wheel debuted in Chicago in 1893, but don't worry — the 150-foot Navy Pier Ferris Wheel is not that old. The views of the city and shoreline from the top are spectacular. For $12, you can ride not only the big wheel but also another Pier attraction, like the Wave Swinger — and still have money left over for Dippin' Dots or Haagen-Dazs.

7. Visit a Museum

You can see SUE the T. rex at the Field Museum; adult admission is $18. Or venture off the beaten path to the International Museum of Surgical Science, where you can view a 500-year-old amputation saw and some of the oldest X-rays ever taken.

8. Drink Scotch

A flight of scotch, that is, at the Duke of Perth. You've heard of Irish pubs, but Duke of Perth is a Scottish pub, with 90 varieties of single malt scotch on the shelves. Flights of three different varieties start around $20 and go up — way up — from there. Another alternative for your $20 is to take a date to the all-you-can-eat fish fry on Wednesday or Friday, a steal at $10.25 each (Sorry, you'll need to scrounge 50 cents out of your sofa cushions for this one.)

9. Ride the L

Riding the venerable rail system anywhere is a Chicago must, and you can get a three-day unlimited pass for $20.

10. Meet Two Famous Chicagolanders

Two $2.25 one-ride L tickets will get you a trip on the Green Line to Oak Park and back. In this village just outside the city's western border, you can tour Frank Lloyd Wright's home and studio for $15.

Oak Park is also famous as the birthplace of Ernest Hemingway; touring the Hemingway birthplace and museum costs $10. Wright's Unity Temple, another popular tour, is $15.

What's your favorite way to spend $20 in Chicago? Please share in comments — it's free!

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Daniel Block

Also Family Sundays at the Cell (White Sox) are great. Tickets as low as $5!, and many at $10.