Chicago is a world-class city that offers much to the budget traveler. This travel guide for how to visit Chicago on a budget will save you time and money. It is an attempt at getting you around this popular city without destroying your wallet. As with most tourist meccas, Chicago offers plenty of easy ways to pay top dollar for things that won't really enhance your experience.
When to Visit
Chicago winters can pack a powerful one-two punch of deep snow and icy winds, so pack accordingly. The weeks prior to Christmas are popular with Michigan Avenue shoppers. Be aware of the city's many festivals and event dates, because fewer hotel rooms and higher prices can result. Book well in advance. Summers are mild but it's not unusual to see multiple days with intense heat and humidity. Early fall might be the best time of year for a visit. Temperatures are comfortable and sunshine is abundant.
Where to Eat
Sports legends Mike Ditka and the late Harry Caray both are associated with excellent restaurants in the Windy City. Neither is exactly a "budget" offering, but they offer unique Chicago dining experiences if you want to invest the extra money. Another great tradition is Chicago-style deep-dish pizza. Be warned: one or two pieces of deep-dish can be very filling. Go a size smaller than the pizza you would order at home.
Open Table is especially helpful in Chicagoland, where more than 10,000 restaurants provide menus and reservation access with just a few clicks. You can find discounts on fine dining during Chicago Restaurant Week each February.
The loop area offers a lot of cheap fast-food places where the prices will be higher than what you're paying at home, but nonetheless affordable. Office workers jam these small restaurants at lunchtime, so plan accordingly.
Chicago offers one of America's best mass-transit systems, with subways in the "Loop" or downtown area, elevated trains (locals call them "the El") and buses. Lines serve both O'Hare and Midway airports and are far cheaper than cab fare. Several free shuttle buses operate along Michigan Avenue. Although there's no fare, it's customary and gracious to tip the drivers. Public transportation tends to operate in a spoke system from downtown into various suburban cities. If you'll be traveling from suburb to suburb in Chicago, it's likely you'll need either a rental car or rideshare service.
Park your car and forget it. Driving from attraction to attraction in the Loop is not recommended. Each parking stop can cost $20 USD or more, and metered spaces along the street can be tough to find. The large Millennium Garage at Columbus and Monroe (Grant Park area) offers day rates that are often lower than what hotels charge for overnight parking, and the area is well-patrolled.
Where to Stay
Michigan Avenue offers fine shopping, dining, world-class museums and free shuttle buses to transport you between attractions. Hotel prices here tend to be high, but Priceline and other discount Internet services often turn up good deals, albeit a block or two from the main drag. Bargains also turn up for hotel rooms near O'Hare Airport, but remember commutes to the center of the city can be an hour or longer at times. Airbnb.com lists an average nightly rate of $122 in Chicago, but a recent search turned up dozens of properties for under $40/night.
Be certain your find is relatively close to public transportation stops. If you want to splurge, a four-star hotel offering good value is the James Chicago at 55 Ontario.
Two passes get much of the attention from Chicago visitors. CityPass and GO Chicago Card offer interesting features that could benefit your itinerary planning.
CityPass offers admission to six Chicago attractions for adults and children 3-11 years old. It's valid for nine days from first use.
Go Chicago Card is purchased prior to your trip and then activated on first use. You can buy from one- to seven-day cards good for free admission at dozens of local attractions. Design your itinerary before you consider a Go Chicago purchase to determine if the investment will save you money on admissions. At times, it will.
Rosa's Lounge on the north side is famous for jazz, but there are scores of clubs that offer the same. Chicago has a vibrant theater community, with several Broadway-quality shows in town at any one time. The Second City troupe was a starting place for some of the nation's greatest comedy acts.
Check out the theater and musical performances at Northwestern University. NU has one of the nation's top-rated university theater programs. Tickets cost a fraction of the prices downtown. The campus is in Evanston, about 12 miles north of the Loop. At the red line El northern terminus (Howard), change to the purple line. If you don't want to go all the way to Evanston, Northwestern has connections with the Looking Glass Theater in Water Tower Works along N. Michigan Ave.
Chicago is a cosmopolitan city, featuring hundreds of ethnic groups. Settlers from many nations made the city great, and it's possible to look around and swear you're in Warsaw, Beijing, Stockholm, or some other distant city. Look for the street festivals and sample the foods!
Looking for the best view of downtown Chicago? You might get wrapped up in the Willis Tower vs. John Hancock Center debate. Willis Tower (formerly known as Sears Tower) is taller and affords a spectacular view of the city and suburbs at night. It also has the Skydeck, a plexiglass ledge that gives the sensation of walking unsupported above the street below. But many prefer the view for the Hancock ("Big John") because of its proximity to Lake Michigan. You'll see more shoreline. Costs are about the same.
Discounts for Great America are possible if you print Six Flags tickets or passes before you leave home. The park is quite a distance (45 mi.) from downtown in Gurnee, about halfway between Chicago and Milwaukee.
Whether or not you're a baseball fan, it's important to experience iconic Wrigley Field. Tickets are not always easy to get for a Chicago Cubs game, especially since the break-through World Series championship season in 2016. But the experience is worth a little added expense. Get there early to watch batting practice at no extra charge. If prices are not to your liking, check StubHub for bargains, especially at the last minute.
Millennium Park on the lakefront was once a dirty rail yard, but planners and philanthropists turned it into one of America's finest urban playgrounds, what some call Chicago's front yard. Concerts and festivals abound here, but it's worth a walk around even if nothing is scheduled. Don't miss Buckingham Fountain. The city's park system is one of the most extensive among the major cities of the world.
Park activities tend to be very budget-friendly, and you can download a smartphone app that will detail what's happening during your visit to various Chicago parks. Search the app store for "My Chi Parks."