To make it in Chicago, even as a tourist, you've got to be a realist. The weather can be wildly erratic, airport cabs are a pain, and business travelers, who are by and large less price-sensitive than the rest of us, rule the tourism business. Knowing the facts will help you work the system to your advantage, whether it's finding the best transportation or snagging a table at the hottest new restaurant.
As locals like to say, if it weren't for February, everyone would want to live here. Hot and humid in summer, cold and windy in winter, Chicago weather wards away the thin-skinned. Fall and spring can be sublime. Or rainy. In autumn, pack for potential rain (collapsible umbrella), cold (gloves) and colder (hat) spells. Plan your wardrobe based on layers that can be peeled or piled as the thermometer demands.
Lodge Off the Beaten Path
The closer you are to Michigan Avenue, the more you'll spend. This goes for almost anything, from shopping and dining to hotels. If you're hunting for a bargain hotel room, look beyond downtown to the Lincoln Park neighborhood, which offers cheapie rooms from chains (Best Western, Days Inn) but doesn't sacrifice location. Downtown hotels, which thrive on business travel, offer better rates, at least on weekends.
Chicago has two airports, O'Hare International and Midway Airport. Both are roughly equidistant from downtown. Midway is more convenient if you're visiting the South Side, O'Hare if you aim for the North Side. Both are connected to downtown via the "el" train system ($2 fares). The Orange Line shuttles between Midway and downtown. The Blue Line runs between O'Hare and downtown. The rides to the airports from downtown take about 40 minutes. Considering that taxis are easily $40 without traffic backups, the "el" is the way to get to/from the airports.
Unless your stay involves extensive visits to the suburbs, don't even think about renting a car in Chicago. Parking rates are exorbitant and parking spaces few. Downtown, the "el" train system ($2 per ride) reaches most of the city's major sights. Taxis are plentiful for quick rides. Lesser known are the water taxis that ply the lakefront and the Chicago River. Shoreline Sightseeing operates water taxi service ($6) from Navy Pier to the Sears Tower on the river, and from Navy Pier to the Shedd Aquarium along Lake Michigan. Operating hours diminish after Labor Day but continue through October.
Don't be surprised if your hotel bill is higher than the per-night rate quoted. The city imposes a hefty 14.9 percent tax on hotel rooms. Sales tax is also higher in the city than elsewhere in the state, running to 9 percent. It's high but useful: double the sales tax on a meal and you have the waiter's tip.
Going to the theater is a must in Chicago, which has a vibrant performance scene. To get bargain seats on the day of the performance, check Hot Tix. The League of Chicago Theaters runs this half-price operation, which announces discounted shows daily at 10 a.m. at its walk-up locations at 72 E. Randolph in the Loop, and 163 E. Pearson in the Water Works Visitor Center.
Passport to Entry
If you intend to see several Chicago attractions in one visit, consider investing in the Chicago CityPass. The $49.50 pass gets you into the Shedd Aquarium, Field Museum, Adler Planetarium, Museum of Science and Industry, and the Hancock Observatory, saving you more than $40 on separate admissions. The pass is good for nine days from its first use and may only be used once at each attraction.
It's a good idea to always make reservations for dinner, especially on weekends. With the exception of Loop pre-theater seatings, which usually require at least a day's notice, you can often make that reservation on the same morning. You'll find the experience far more enjoyable with just a day or two of advance planning.