Chicago Hotel & Accommodations Guide

As a major city with a thriving tourist industry, Chicago is practically overrun with hotels, especially in the downtown area. High demand keeps the prices from coming down too low, but you can often score a deal, particularly from October to April (except for the holidays) when temperatures are lower and fewer visitors come to the city.

Which area to stay in?

Most visitors to Chicago stay in one of two areas: downtown in the Loop, or just north of the Loop (over the Chicago River) on or near Michigan Avenue. Both areas are ideal for visiting the most popular sites, like Museum Campus, the John Hancock Building, Willis Tower, Grant Park, Navy Pier, and the Magnificent Mile.

One downside (or upside, depending on your view) to both locations is that they become very quiet after working hours and on weekends. While there are lots of quick-serve restaurants popular with the workforce during lunch hours, lots of post-work happy hour spots, and lots of swanky hotel lounges and restaurants, there aren’t many places frequented by locals around here. Most Chicago residents live in one of the less-touristy neighborhoods like Lakeview, Lincoln Park, Bucktown, Logan Square, etc. They then enjoy the nightlife in their local area. The bars and restaurants in these ‘hoods are generally cheaper and less touristy.

If you want to experience the city from more of a local’s perspective and be close to the best nightlife and dining, Lakeview and Bucktown are ideal places to stay. Those attending a baseball game at Wrigley Field can find inexpensive accommodation near the stadium, in Wrigleyville.

Cheapest hotels in Chicago

There are only a few hostels in Chicago and they offer both cheap dorm accommodation and private rooms for the budget traveler. Cheap and mid-range hotels are located in the Loop, South Loop, and Lakeview areas and generally offer accommodation that is clean and comfortable but no-frills. If you don’t plan on spending much time in your room, these hotels will be more than adequate. During less-popular times of the year, you can often find 3 and 4-star hotels deeply discounted as well.

Luxury hotels

Chicago is home to several luxury hotels like James, the Four Seasons, and the Peninsula. While these hotels often offer spectacular views and excellent service, they can be very expensive, especially during peak season. If you’ve got the cash or are celebrating a special occasion, they are definitely worth the price though.

Staying near the airport

Unless you have a very early flight out of Chicago the next morning, I do not recommend staying near the airport. While hotels near O’Hare and Midway can be cheaper, the hassle of getting back and forth to the city each day via the blue line (a 30-45 minute ride) or driving in (and dealing with costly and hard to find parking) is not worth the savings.

Most visitors to Chicago will stay in a hotel, usually one located in the heart of the tourist sites, near the Magnificent Mile. But these highrise hotels aren’t your only lodging option. Here are a few hotel alternatives for your stay in Chicago.


Chicago is home to just a few hostels, which offer both private rooms and dorms. If you are traveling solo, these are great budget-friendly places to stay and to meet other travelers. But if you have a group of three, you’d be better off getting a low-cost hotel room and ordering a roll-away bed, or getting two queens and having two people share. For groups of two, do a little price comparison. During high-season, a hostel with a private room may be a cheap option, but during off-peak times you may be able to snag a 2- or -3star hotel for less than the cost of a hostel room.

B&Bs & Guesthouses

Many people don’t realize that there are bed and breakfast and boutique hotel/guesthouse options in Chicago. While some of these can cost just as much as a fancy hotel, others will cost less than $100 per night. And all of them offer a few perks that the downtown hotels don’t. Chicago’s B&Bs are located outside of the downtown area, in neighborhoods like Lakeview, Wrigleyville, and Bucktown, so you can get a better glimpse of life in Chicago. You’ll get personalized attention and recommendations from the owners, plus, breakfast is included so you’ll save even more.


If you’ll be staying more than a few days, it can be well worth the extra effort to book an apartment for your stay. Though there’s often an extra fee involved (either a deposit or a cleaning fee) and checking in is sometimes not quite as easy as rolling up to a fully-staffed hotel, you can often save a considerable amount of money by staying in an apartment. You’ll have more space and access to your own kitchen so you can cook meals on occasion. Choose a place located near an el line and you’ll be able to get anywhere in the city with minimal effort.

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