My Activity & Trips
The shoulder seasons of April–May and September–October are the best times to get great deals on Chicago hotels. During these times of the year, you can avoid the huge tourist crowds and still enjoy pleasant weather for exploring the city. If visiting during these months, you can also take advantage of fun-filled festivals such as Mayfest, the official start to Chicago's festival season, Hyde Park Jazz Festival, and Chicago International Film Festival.
Even better deals for hotels in Chicago can be had from November through March, but you’ll pay the price with biting cold weather. Some exceptions do pop up around special events such as the McDonald’s Thanksgiving Day Parade and February’s Chicago Auto Show.
Chicago has several truly elite hotels with world-class service. The Langham, Chicago and The Peninsula Chicago are two outstanding five-star options. Both offer high-end spa services, modern fitness centers with in-house swimming pools, and elegant dining options.
For the savvy business traveler looking for a luxury hotel at a slightly more budget-friendly price, Thompson Chicago Hotel, is an excellent four-star option. Thompson Chicago offers state-of-the-art facilities and packages catering to the business traveler.
From the affordable Inn of Chicago to national chains like Travelodge Hotel Downtown, Chicago has many budget-friendly options that won’t break the bank. Both of these hotels are located in the heart of downtown Chicago, making either the perfect option for the business traveler or the tourist. Clocking in at well under $100 per night, these clean and simple properties still offer guests a decent array of amenities, including on-site dining options.
If you’d rather avoid the crowds of downtown Chicago but still enjoy a budget-friendly private room and a vibrant neighborhood, look at some of Chicago’s trendiest, more residential neighborhoods. Options include Days Inn Chicago in eclectic Lincoln Park.
Cheap hotels in Chicago abound, however even the cheapest hotels may be beyond the budget of many travelers. If this is the case, consider a hostel. Hostels are highly social environments hosting guests from all around the world. Rooms are normally dormitory style, equipped with bunk beds and lockers for your valuables. Common lounges, communal kitchens, and the shared sleeping spaces offer a great way to meet people and save money. Hostels can be found all over the city, from the downtown area to suburbs further afield. Some excellent hostels are Holiday Jones, a hostel with a boutique hotel feel only 10 minutes from downtown; Wrigley Hostel in Wrigleyville, the party center of Chicago; and Urban Holiday Lofts, located in a renovated 100-year-old warehouse.
Chicago home shares and rentals offer a truly unique way to explore the Windy City. With hundreds of listings on Airbnb, there is something to suit almost any budget. Options range from shared rooms/sofas outside the city center for under $40/night to private rooms in shared homes for well under $100. Excellent deals can be had on entire apartments, some offering high-end finishes with sweeping views of Lake Michigan for under $200. The room share or home share options allow guests to live with locals and get an insider’s look into life in Chicago. Plus, access to a kitchen and the ability to cook your own meals can really keep costs down.
Airport hotel options in Chicago, at both O’Hare and Midway, are similar to what you will find in many other cities throughout the United States. Properties here consist mostly of international chains focused on business travelers, such as Hilton Chicago O’Hare*, Four Points by Sheraton Chicago O’Hare*, Hilton Garden Inn Midway Airport* and Sleep Inn Midway*. All of these cheap hotels are located within minutes of airport terminals, making for an easy way to catch those early morning flights.
As with other cities, go a bit farther from the airport and you will find even cheaper hotels and motels, such as Skylark Motel* for Midway or Prime Motel* for O’Hare. These places are basic, but offer bargain basement prices and are relatively close to the airports.
Also known as the Magnificent Mile or The Loop (thanks to the loop that the "L" train lines make as they circle downtown), downtown is definitely the neighborhood to stay in for the business traveler. With easy connections to both O’Hare and Midway Airports, this area is not only the beating heart of Chicago business, it also has plenty of activities to help business travelers kill time between meetings or unwind after a stressful day.
Options include activities along Lake Michigan’s shoreline, the Navy Pier, The Art Institute of Chicago, Millennium Park, and theaters such as the Steppenwolf. The area also offers a nearly limitless array of dining and nightlife options from dive bars to Michelin-starred dining.
Lincoln Park, home to Lincoln Park Zoo, is a vast park that borders Lake Michigan and has given its name to the surrounding community area, which stretches inland from the park’s western border. The community area encompasses a number of small neighborhoods, together creating an eclectic and vibrant area north of downtown. DePaul University is located here, so you can find inexpensive restaurants, cafés, and bars all around the area, along with a number of music venues. Of course, you can also find upscale national retailers and high-end boutiques. Nightlife options are fun, lively, and varied.
Located south of the downtown area, this neighborhood and community area is home to the prestigious University of Chicago. This area offers up an array of activities for those who like to enjoy nature, with Lake Michigan to the east, Midway Plaisance (a long, narrow park area sandwiched between streets) to the south, and Washington Park to the west. Hyde Park is also famous for several reasons. Midway Plaisance was the home of the first Ferris Wheel, erected when Chicago hosted the 1893 World’s Columbian Exposition. In more recent years, the neighborhood has gained fame as the home of the Obamas. As with Lincoln Park, there are many inexpensive and high-end retailers, boutiques restaurants, coffee shops, and nightlife options to be found.
Chicago’s public transit system makes it easy for the independent traveler to navigate the various neighborhoods and sites around the city. However, for those travelers short on time or who wish to get a bit of a history lesson with their sightseeing, Chicago’s tour companies offer many excellent choices. The international Gray Line tour bus company operates here, with various “loops” on offer. If you want something more local, try one of the many bicycle tours here that showcase not only downtown but also neighborhoods like Lincoln Park, Hyde Park, and others. Finally, don’t forget about the river. Cruise operators offer tours covering Chicago’s architecture and history or a lovely sunset dinner cruise. Check with your hotel, the tourism center, or just hit the streets with an open eye.
The “L” is Chicago’s metro train system, a mix of underground subway and elevated tracks. The "L" is inexpensive and easy to use with eight color-coded lines that all converge in downtown Chicago before branching out north, south, northwest, west and southwest to cover the major neighborhoods and suburbs.
The blue line can take you from O’Hare Airport all the way downtown and then west to Forest Park. The Orange Line starts at Midway Airport and ends downtown, where it connects with the other seven lines. Use the "L" to get to trendy neighborhoods such as Lincoln Park or Hyde Park, as well as Loyola, The University of Chicago, and U.S. Cellular Field for the White Sox.
The only direct north-south options on the "L" system run right along the lakeshore through downtown. If you want to go from north to south without going through downtown, take advantage of Chicago’s vast and reliable bus network. The bus system will easily get you everywhere the "L" train can’t. It’s slightly cheaper than the "L" and sometimes may be an easier option for shorter distances. Plus, with more frequent stops and street level views, it may be easier for newcomers to find what they’re looking for.
Rush-hour traffic in Chicago can be an absolute nightmare, and parking in popular neighborhoods can be difficult, time consuming, and expensive. It all gets worse during Chicago’s notoriously harsh winters. Leave the car at home and use public transit or hail a passing taxi when the mood strikes. Uber, Lyft, and other ride sharing options are also available. It's best to leave the car at home.
© 2017 Hipmunk, Inc. Hipmunk is a trademark of Hipmunk, Inc.
© 2017 Hipmunk, Inc. Hipmunk is a trademark of Hipmunk, Inc.