Where to stay in Chicago

One of the most challenging things to figure out when planning a sports road trip can be where to stay. Should you stay near the stadium? Downtown? What if the stadium is in a suburban or industrial area? Would you even know? It can be pretty confusing, especially if you don’t know the area well. This chapter will tell you everything you need to know about your lodging options for visiting Guaranteed Rate Field.

Should you stay near the stadium?

First, let’s review where Guaranteed Rate Field is located. It’s in Bridgeport, a working-class neighborhood about 5-7 miles south of downtown Chicago. Without traffic, it’s less than a 20-minute drive from pretty much anywhere downtown, and it’s not much slower to get to by subway once you’re actually on the train.

While Bridgeport itself is a decent place, the South Side of Chicago, in general, is not the best area to stay. The lodging options are minimal, the crime rate is higher, and most of the sights to see in Chicago are downtown or on the North Side. We consider Guaranteed Rate Field to be a safe place to visit for baseball, but it’s not an appropriate place to stay while you’re visiting Chicago. You’re much better off being more centrally located to the things you’ll want to do and see in the city, which means you should be looking to stay in the more typical tourist areas of Chicago – downtown/the Loop, Near North (which consists of the River North, Streeterville, and Gold Coast neighborhoods), and West Loop.

Overview of the different neighborhoods to stay in

As we mention in the Local Transit chapter, picking a place to stay will be strongly connected to your stadium transit strategy. If you are planning to use public transportation to get to Guaranteed Rate Field, then you’ll want to stay at a hotel that is convenient to the Red Line of the subway system. It’s the easiest and most direct way to get to the stadium. 

On the other hand, if you’re planning to drive or take a taxi/rideshare to the stadium, then there are additional hotel zone options, such as the West Loop, as well as hotels in the other zones that are a further walk from the subway line. Some neighborhoods and hotels are just more conducive to public transportation, while others will only be conducive if you’re traveling by car. 

Here’s an overview of the neighborhoods you should consider for your visit.

NOTE: Depending on who you ask, you can get different boundaries for different neighborhoods. The reality is that the lines between Streeterville, River North, and Gold Coast really don’t matter very much. These are all neighboring areas that are very similar to each other. 

And keep in mind: if an attraction is in The Loop, that may mean that it’s just a 5-10 minute walk from River North. Downtown Chicago is a relatively small place. The distance from the north end of the Gold Coast to the southern end of the Loop is just two miles.

The Loop/Downtown

What’s there: Willis Tower, theater district, Millennium Park, Grant Park, Buckingham Fountain, Art Institute, Riverwalk

Distance to Guaranteed Rate Field: 4-5 miles, 15-30 mins by car, 20-25 mins by subway (once you’re on the train, including walk to ballpark)

Downtown Chicago, which is also known as “The Loop”, is the city’s central business district. It’s home to plenty of points of interest, including: most of Chicago’s major performing arts centers (Nederlander Theatre, Cadillac Palace Theatre, CIBC Theatre, Chicago Theater, Auditorium Theatre, the Lyric Opera), the Willis (formerly Sears) Tower, Millennium Park and the “Bean,” Grant Park, Maggie Daley Park, Buckingham Fountain, the Art Institute of Chicago, the Chicago Riverwalk, and Macy’s on State Street. The Loop will have fewer restaurants than River North or the West Loop, but it will also be closer to Chicago’s Museum Campus (Field Museum, Adler Planetarium, Shedd Aquarium, Soldier Field). 

The Loop is bustling during the day, but much quieter at night, as there isn’t a ton of residential housing in the area – there’s much more of a residential presence in River North. There’s nothing wrong with staying in The Loop – it’s easily accessible to the subway, and a quick walk across the bridge to River North as well. 

There are three Red Line subway stations in The Loop: Lake Street, Monroe Street, and Jackson Blvd.

Lake Street is the closest to the river and the bridges leading to River North, so if you’re someone who likes to walk and wants to explore on foot, staying at a hotel closer to the river and the Lake Street station will be the best call.

The Monroe Street station is along State Street where the majority of Loop retail establishments are. Retail in the Loop is not as nice as it is in River North along Michigan Avenue, but it’s here if you wanted it. The Monroe Station will be closer to the heart of Grant Park and Buckingham Fountain, but we’d still suggest staying closer to the river.

The Jackson Blvd stop is our last choice of the three. As you go further south, we think the potential safety issues go up after dark. There’s less retail and fewer restaurants, but more iffyness. 

In terms of safety, The Loop is safe during the day and completely appropriate for tourists to be wandering around. At night, the area around Lake Street will often have a lot going on, even during the week, with the theater district and more restaurants located up there. The areas around Monroe and Jackson will be significantly quieter, and not in a good way.

One more thing to consider is airport transit. One of the other benefits of staying in The Loop is that the subways to O’Hare and Midway both run from this area. The Blue Line to O’Hare has stations at Clark/Lake and Washington, which are both close to the Lake Red Line station. And there’s a Blue Line stop at Monroe and Jackson as well. But once again, from a safety perspective, we prefer the Clark/Lake and Washington stops over the ones further south.

If you’re going to Midway, the Orange Line has a stop one block away from the Lake Red Line station, plus multiple stops running south on Wabash Street, parallel to the park. 

So, in terms of public transit, the Loop gives you access to both airports, plus Guaranteed Rate Field (and to Wrigley Field as well).

Pros

• Most convenient for public transit to airports and ballparks
• Closest to the Theater District
• Walkable to River North

Cons

• Fewer retail and dining options
• Quieter at night
• Less safe at night as you go further south, and… 
• Not as pretty as River North.

Near North

The Near North neighborhood is actually made up of three neighborhoods: River North, Streeterville, and Gold Coast. River North and Near North will often be used interchangeably to mean the same thing, but to avoid any confusion, this is the correct definition.

River North

What’s there: Magnificent Mile shops, tons of restaurants, the Wrigley Building, John Hancock observation deck, Water Tower

Distance to Guaranteed Rate Field: 5-6 miles, 20-30 mins by car, 25-30 mins by subway (once you’re on the train, including walk to ballpark)

River North is the heart of Chicago’s tourism industry, with the greatest concentration of hotels in any of our hotel zones, and most of them will be convenient to the Red Line. All of the hotel brands you’d expect to see are there, including everything from budget level properties to luxury brands. You’ll also be located near tons of restaurants, bars, retail shops, and tourist attractions, including the original Pizzeria Uno and Lou Malnati’s, Portillo’s Hot Dogs, Eataly, Water Tower, the architectural boat cruises, the Wrigley Building, Magnificent Mile, and the John Hancock building.

There is simply a ton to do in River North, including just walking around. And there’s no question that it’s the most popular and most obvious hotel zone for a visit.

In terms of transit, there are two Red Line stations in River North: one at Grand Avenue and one at Chicago Avenue. We need to be honest: the area around the Chicago station can be a little sketchy. It’s not the entire neighborhood – it’s literally just the block around that entrance. There’s a McDonald’s there that has historically been the center of some trouble, and there have been other random instances of crime there.

Now… I’m not saying you need to avoid the station completely. And during daylight it’s much less of an issue. But at night, if you’re getting off at the Chicago stop, you should be vigilant and attentive. Pay attention to your surroundings, and walk with purpose. This is not the right place for leisurely strolling after coming back from a Sox game. 

In terms of getting to the airport, River North is not convenient to either the Blue (O’Hare) or Orange (Midway) lines – those both run from The Loop. You can take the Brown line into the Loop, or hop on any number of buses, which are absolutely safe and appropriate for tourists, and then transfer from there. It’s not particularly difficult – the Chicago subway system is hardly overwhelming in terms of trains and its map, and as long as you know what bus you’re getting on, it’s not that hard either. It’s just that it can be intimidating to people who are unfamiliar with it, and carrying luggage makes it even more trying. 

If you do want to do this, Google or Apple maps can help you figure out what trains or buses to take, and they are both accurate. You can also download the free Citymapper app, which is also quite good.

Pros

• All the foods
• All the shops
• Tons of hotels
• The pretty part of downtown

Cons

• Hotels can be more expensive
• Not directly connected to airports via subway

Streeterville

What’s there: Museum of Contemporary Art, Navy Pier, Lake Michigan, Lake Shore Drive walking/running/bike path

Distance to Guaranteed Rate Field: 6-7 miles, 20-30 mins by car, 10-15 minute walk to Red Line station and then 25-30 minutes to ballpark (including walk to ballpark)

Streeterville is a completely fine area to stay in, but it has fewer restaurants, bars, and retail shops than River North. It’s home to Northwestern University’s Hospital campus, as well as Navy Pier and the Museum of Contemporary Art. It will be quieter and have less foot traffic than River North, which can either be good or bad, depending on what you’re looking for. Streeterville is also going to be a further walk to the subway than River North. On the other hand, if you’ve decided to take rideshares or taxis to the ballpark, it’s actually an easier trip than from River North because you’re right at Lake Shore Drive, which is often the fastest route to the stadium.

But Streeterville is also right up against Lake Michigan, and the walking/running/bike path that goes along the entire lake. It’s a fantastic area, and one we’d highly recommend checking out. You can start from Streeterville and walk all the way up to Lincoln Park to check out the Lincoln Park Zoo, Botanical Gardens, Oak Street Beach, and North Avenue Beach. If you’d like to bike it, Chicago’s Divvy bike share program is easy to use – download the app and you’ll see the locations and fare info.

Note: when we call this a “different neighborhood” than River North, understand: you’re a 5-10 minute walk from being in the heart of River North. If you can find a good hotel option in Streeterville, don’t hesitate to take it.

Pros

• Proximity to Lake Michigan and River North
• Quieter than River North

Cons

• Further walk to the Red Line
• Quieter than River North

Gold Coast

What’s there: Gibson’s steakhouse, Lincoln Park Zoo (just north), upscale/luxury restaurants and shopping

Distance to Guaranteed Rate Field: 7-8 miles, 25-30 minutes by car, 10 minute walk to Red Line station and then 25-30 minutes to ballpark, including walking time to the stadium

Gold Coast is a beautiful area of the city. It has plenty of upscale restaurants, classic dive bars and luxury retail shops. Rush and Division Streets are home to a bunch of cheesy bars that you’ve probably seen featured in cheesy movies about Chicago, going all the way back to 1986’s “About Last Night”. Oak Street is Chicago’s mini-version of Rodeo Drive (I’m being very generous here), and the heart of Gold Coast has one of Chicago’s most famous steakhouses, Gibson’s. 

You’re going to pick up on more of a local flair up here as it’s an area that people actually live in. It’s an easy walk to the shops and restaurants in River North, and a great spot if you want to access the walking path along Lake Michigan that heads up towards Lincoln Park and the Lincoln Park Zoo.

In terms of getting to Guaranteed Rate Field, both the Chicago and Division Red Line stops are close by.

For getting to the airports, like River North, you’d have to head down to the Loop to transfer to the Orange Line for Midway, but from this far north, you’d likely head west to pick up the Blue Line at the Division stop in Wicker Park to O’Hare. Honestly, if you’re staying in Gold Coast, take a rideshare and save the hassle. 

Pros

• Great area
• Great restaurants
• Close to the lake, shopping

Cons

• Further away from the ballpark
• Not good for getting to the airport via subway

West Loop

Distance to Guaranteed Rate Field: 5 miles, 20-25 minutes by car. Getting to the ballpark via subway… is complicated

What’s there: United Center (Blackhawks, Bulls), Fulton Street Market, Time Out Market, McDonald’s global menu, great restaurants, bars

The West Loop once upon a time was an industrial district, but it’s long been home to some of the best restaurants in Chicago. And in the last decade, several Fortune 500 companies have moved into the West Loop district, including Google and McDonald’s, which has subsequently drawn more residential development, which has drawn more restaurants, bars, and retail. 

Some of the cool things that are in the West Loop are the Time Out Market, a food court of local Chicago favorites, and you can also head over to McDonald’s headquarters to their first floor restaurant. Why make a special trip for a McDonald’s? Because they serve items from around the planet here on a rotating menu. Want to try a Grand McExtreme Intense Cheddar? This is the place!

If you want more of “the scene” in terms of bars and restaurants, the West Loop is a good place for you. But it’s definitely further removed from many of Chicago’s sights, so to do those will take more time and cost in terms of transit. And you don’t really need to stay in the West Loop to experience these things: it’s just as easy to rideshare over there from the Loop, River North, Streeterville, or Gold Coast.

In terms of transit to Guaranteed Rate Field, this is where it’s a little complicated. The Green Line runs from this area straight to the ballpark… albeit a handful of blocks east of where the Red Line station is. What’s the difference between a couple of blocks, you ask? Well… it can be a lot. During the day, the difference isn’t that great. But at night, we have a much harder time recommending that you walk to the Green Line for safety reasons. And to take the Red Line back to the West Loop would require a transfer to the Green Line once you get to the Loop.

Honestly, we don’t love it. So our advice: if you’re going to opt for the West Loop, go ahead and commit to taking rideshares or taxis to the ballpark – particularly on the return trip.

Pros

• Some of the best bars and restaurants in Chicago
• Close to the United Center, if you’re visiting during NBA/NHL seasons

Cons

• Farther from downtown Chicago and most attractions
• Transit is more complicated
• Less safe than other areas

Bottom line for picking a hotel

There are dozens to choose from, and there will be multiple options that meet your needs. Our best advice is:

1. River North and Gold Coast are the nicest areas and convenient for getting to the ballpark via the subway 
2. If you’re going to use public transit to get to Guaranteed Rate Field, find a hotel that is within 4-5 blocks of a Red Line station 
3. If you’re using public transit for getting to the airports, find one that is close to the Blue Line for O’Hare, or the Orange Line for Midway.