Traveling to Chicago

If you’ve never traveled to Chicago before, then you may have some questions about the best way to get here, and how to get around Chicago once you’ve arrived (including how to get to/from the ballpark). This chapter will cover advice on how to get to Chicago, and how to get from the airport to your hotel, while the chapter on “Local Transit” will deal with how to get to and from Wrigley Field. 

Even if you have been to Chicago before, our tips on getting around will help make your trip as easy and enjoyable as possible. 

Below, we’ll cover:

• Flying to Chicago
• Transportation from airports to the city
• Car Rental
• Amtrak
• Metra

Flying to Chicago: Midway and O’Hare airports

Chicago has two airports: O’Hare International Airport (ORD), which is 18 miles northwest of downtown (13 miles from Wrigley Field), and Midway International Airport (MDW), which is 12 miles to the southwest of downtown (18 miles from Wrigley Field). (If you’re looking at Google Flights right now and it’s telling you that Chicago Rockford International Airport is in Chicago, trust us: it absolutely isn’t. That airport, despite having “Chicago” in its name, is actually farther away from Chicago than Milwaukee’s airport is).

From either MDW or ORD, it will take you between 30 minutes (no traffic) and 90 minutes (terrible traffic) to get downtown by car. You can also take the subway (known as the “L”) to The Loop (Chicago’s central business district), which will take you about 35 minutes from Midway, and 45 minutes from O’Hare once you’re actually on the train.

The only airlines that service Midway Airport are Allegiant, Avelo, Delta, Frontier, Porter, Southwest, and Volaris, with Southwest carrying about 95% of the passengers who travel through it. Midway is one of Southwest’s biggest hubs, with direct flights from over 70 cities, including 24 MLB cities. So your chances of finding a flight on Southwest to Chicago are really good.

Meanwhile, Delta, Frontier, Southwest, and Volaris also fly into O’Hare, along with most other airlines including United, American, Spirit, and JetBlue. O’Hare is a hub for both United and American, and an operating base for Spirit, so those three airlines alone will probably connect you from just about anywhere you might be coming from. And because of Chicago’s central location, getting an evening flight to just about every corner of the US is very possible, which will make seeing a Sunday afternoon game at Wrigley Field viable if you still want to get home Sunday night.

Which airport to choose: O’Hare or Midway

In general terms, it doesn’t matter which airport you fly into, since they are both about the same functional difference from the majority of the hotels that you are likely to be staying at while you’re here. If you’re staying in River North or the Loop, then the difference between the two is negligible. 

But, O’Hare’s proximity to the ballpark does have one strategic advantage, and that is if you are going to fly into Chicago right before a game, or out of Chicago following a game. In that case, O’Hare is significantly closer and could make a real difference in your ability to make the game or catch a flight. 

Why? Because even though you can’t take your luggage into the stadium, there are two baggage storage companies that operate within two blocks of the ballpark. For a $6-10 fee per bag, you can store your luggage from as early as 9am to one hour after the game ends. Which means you could land at O’Hare at 11:30am and likely be in your seat for a 1:20pm first pitch (especially if you aren’t claiming luggage at the airport), and you could leave Wrigley at 4:00pm and be at O’Hare in time for a 6:30pm flight. There would be no need to go to your hotel to store or pick up bags, easily saving you an hour or more. For more detailed information about luggage storage at the ballpark, check out our Lodging chapter.

So if your plans do include going directly to/from the airport to/from Wrigley Field, booking a flight from O’Hare can make a real difference and we’d highly recommend looking into it. But if you’re not as pressed for time as that, or your flight schedule won’t allow for it, then Midway is a completely acceptable option.

Transportation from airports to the city

TSI airport transportation advice: Stick to public transportation or rideshare/taxis

For visitors that are flying to Chicago, The Stadium Insiders recommend either taking a taxi or rideshare to your destination, or taking the subway. There are no public buses that will go from the airports to tourist areas, and hotel shuttle services from the airports are far more expensive than rideshares or taxis. There are no downtown hotels that offer airport shuttles.

We don’t recommend renting a car unless you have a specific need for one. If you’re staying in the city, public transit is abundant and easy. Cars are expensive to rent, expensive to park, and will just add aggravation, cost, and inconvenience to your experience if you’re staying near the city center. If you prefer to avoid public transportation, you’ll find your visit will be much much easier by just sticking to rideshares and taxis.

Taking a taxi/rideshare from the airports

This is the easiest of your transportation options, and certainly the most popular. The Stadium Insiders specifically recommend taking a taxi or rideshare when:

• You want the easiest and most direct experience.
• You have a lot of luggage.
• You aren’t enthusiastic about public transportation and would feel more comfortable in a car.
• You are traveling during non-rush hour times, when traffic between the airports and downtown won’t be so bad. The subway will take an hour plus, while a car could take as little as 30 minutes without traffic.
• You are traveling either early in the morning or later in the evening (before 7am or after 8pm): it is just a safer option than the subway during off-hours (note: this only applies to transportation to/from the airport. This is a completely different issue for transportation to/from the ballpark, which will be discussed later).
• You are staying in the areas to the north of downtown Chicago (River North, Streeterville, Gold Coast, Lincoln Park, Wrigleyville). To get to these locations via subway, you would need to transfer from one subway to another (or a bus) once you arrive downtown, and if you haven’t been to Chicago before, this may be more than you’re willing to deal with while toting luggage.

A rideshare to the downtown area from O’Hare will take approximately 35 minutes (off hours, no traffic) to no more than 90 minutes (worst traffic possible) at a typical cost of $35-50, and from Midway will take approximately 30 minutes (off hours, no traffic), to 75 minutes (worst traffic possible) at a cost of $30-40. Surge pricing may (and often will) inflate these costs.

TSI TIP: A taxi will obviously take a similar amount of time, but will be at a more consistent rate of $45-55 from O’Hare and $40-50 from Midway. Check your rideshare app to see what the price of your trip will be when you’re ready to leave. If it’s more than the cost of a taxi, then opt for the fixed price of a taxi. There are marked taxi stands at both airports that are easy to find. 

But we will note this: once ridesharing moved into the airports, the supply of taxis has definitely decreased. If you’re arriving at the airport during a busy time, there could be a line at the taxi stand and you might have to wait a bit. There’s no question that rideshare is the more reliable method of transit, so if the fare is close, opt for rideshare.

Public Transportation – When to take the subway

If you’re curious about the subway, you might find that it can be an excellent transit solution. There are several reasons why you would consider taking the subway from the airport to your lodging destination:

• You’re looking to save money. A taxi/ride-share to downtown will cost anywhere between $30-55, while the subway to downtown will cost $2.50 from Midway or $5.00 from O’Hare per person.
• It’s rush hour and your navigation app says that traffic will take more than 90 minutes in a car.
• You are staying at a hotel in The Loop which is located within walking distance of a subway station. 

The actual subway ride from either airport to the Loop will take approximately 35-45 minutes once you’re actually on the train. 

Of course, it will take longer to get to your actual destination from the subway station, so you’ll need to factor that into the equation. If you’re staying in the Loop, then you might only need to add another 5-10 minutes of walking time. If you’re staying in River North, Streeterville, or Gold Coast, then it could take you another 15-30 minutes, depending on how you get from the station to your hotel (i.e. transfer to another subway, bus, rideshare/taxi, or walk). Overall, we’d say that if you’re staying in one of these areas, opt for the car ride instead of the subway.

TSI commentary on subway safety

I’ve been living in Chicago for 25 years, and am a devotee of the public transportation system. I use it everyday, and it’s my primary method of transportation both around the city and to/from the airports. And while I’ve seen a thousand colorful things on the subway over the years, I’ve always considered it to be safe. 

But… in recent years (post-Covid), with ridership down and various social issues taking place in Chicago, I’d be remiss if I didn’t say that the system feels less safe to me than it previously has, particularly on the south side (between downtown and Midway Airport). So while I’d love nothing more than to wholeheartedly endorse the subway for getting from Midway to downtown, which I’ve taken hundreds of times, in good conscience I just can’t right now (in 2024). Even in the middle of the day there may be instances where you may not be as safe as you ought to be. 

As for the Blue Line to O’Hare, I do think it’s safe, but issues with homelessness have crept in, and there’s the chance that you’ll encounter some people and/or some odors that might make you uncomfortable. For the most part, the easy fix to that is to simply change train cars at the next station, and that will likely solve the problem. 

So if you’re coming from Midway, I’d recommend a taxi or rideshare for the time being. For O’Hare, the train is still a viable option if it’s convenient for you. But we will update this information as things change.

But if you do take the subway, here’s how

If you opt to take the subway from O’Hare, it’s fairly straightforward: there is only one subway line that goes to O’Hare, and that’s the Blue Line, and O’Hare is also the end of the Blue Line, so it only runs one way from O’Hare, and that is towards downtown. 

If you opt to take the subway from Midway, it’s also fairly straightforward: there is only one subway line that goes to Midway, and that’s the Orange Line, and Midway is also the end of the Orange Line, so it only runs one way from Midway, and that is towards downtown. 

TSI TIP: You can purchase a one or three-day travel pass, good for unlimited rides on the subway and bus system, for $5 and $15, respectively. With the exception of the $5.00 fare from O’Hare, each individual subway trip is $2.50 (which includes two additional rides within two hours), so do the math on whether or not a multi-day pass is worth it. But note: 3-day passes can only be purchased at the airport transit kiosks. They cannot be purchased at stations other than the airport.

If you’d prefer to just use your chipped credit card to access the system, you can do so by tapping it on the card reader. But you’ll pay the standard one-way fare instead of the multi-day discount fare, and you won’t get the free two-hour transfers. 

If you are going to take the subway from downtown to Wrigley Field, or anywhere around the downtown area for sightseeing, then you should purchase the three-day pass — it will absolutely be worth it. But note: each person in your party will need their own multi-day pass.

For information on planning your subway trip, click here for Chicago’s official transit site.

GoogleMaps will also allow you to plot your route using the L.

Should you rent a car to get to Wrigley Field?

For visitors arriving by air, The Stadium Insiders recommend against renting a car for a Wrigley Field visit, unless you have other specific plans that would require one. Some of those reasons are:

• Picking up and dropping off a rental car will add an hour (or more) to your experience each way. Both airports require shuttle rides to their off-site rental car centers.
• Parking at downtown hotels is expensive – it could be as much as $60/night.
• Once you are downtown, your need for a car will be minimal: most attractions will either be within walking distance or a short bus/subway/rideshare from your hotel. 
• Parking at those attractions will also be expensive, and driving/parking will take you longer than just jumping in/out of a rideshare. 

If you DO need a car for a specific excursion beyond downtown Chicago, you should still consider taking public transportation/rideshare/taxi from the airport to your hotel, and then renting a car from a rental location near your hotel. There are several to choose from, and by doing so, you’ll avoid the expense of having to park the car overnight (assuming you are able to return the car to the rental agency before they close, which could be early at downtown locations). Rental cars from downtown locations can also sometimes be less expensive because they aren’t subject to airport taxes/fees.

One other option to consider if you need a car in Chicago is Zipcar. It’s a service that positions cars in garages all around the city, and using your membership ($90 per year), you can reserve any of those cars for as little as $11/hour (or $80/day), which includes all fuel, insurance, and 200 free miles per day. It’s really easy: you just walk up to your car, unlock it using the app, hop in and go. And when you come back, you’ll park it right back where you picked it up, lock it, and walk away. Yes, the $90 membership fee is a lot if you’re just going to use it this one time, but if you have travels to other cities where Zipcar operates, it can be a very useful service.

Check here for more details on Zipcar pricing.

Getting to Chicago by Train

Amtrak

Chicago is one of the most popular train destinations for Amtrak, with 13 different routes that either originate or pass through the city. Obviously this won’t be a primary mode of transit for most people, but for those in cities such as St. Louis and Milwaukee, Amtrak is a great way to get to Chicago for baseball. There’s a train from St. Louis that arrives at 1:40pm, which is perfect for catching a night game, and from Milwaukee there are multiple trains that will get you into Chicago for either a day or night game.

Amtrak services Union Station, which is on the West Side of the downtown area. It’s easily accessible by rideshares/taxis or the bus, and is safely walkable from the closest subway stations (the Clinton station on the Green Line, and the Quincy and Washington/Wells stops on the Brown/Purple lines). You could get in a rideshare/taxi and be at Wrigley Field in as little as 20 minutes without traffic, or maybe 30 minutes in terrible traffic, and don’t forget: they have luggage storage near the ballpark, so you could head directly to the game from Union Station.

Getting to Chicago by train (METRA)

If you’re traveling to Chicago from within the extended Chicagoland region, Metra may be your best option. Metra stops at the Ogilvy Transportation Center, which is a few blocks north of Union Station. For information on Metra, click here.

Bottom Line

If you’re planning on staying in The Loop or the hotel zones to the north, O’Hare and Midway are pretty much similar choices, unless you want to go straight to the ballpark from the airport. In that case, you’ll want to fly to O’Hare, and remember, there’s baggage storage options near Wrigley.

The easiest and fastest way to get from the airport to/from your hotel is going to be via taxi or rideshare. If you’re staying in a hotel in the Loop that is close to an Orange Line (Midway) or Blue Line (O’Hare) stop, then taking the subway may make sense. But if you’re staying in River North, Streeterville, or Gold Coast, or in the Loop further away from the subway, a car is going to be a significantly easier experience, even if it costs more money.

In terms of taking the train to/from Midway, we would caution you that the subway has been iffy on the safety side in recent times, and while the odds are overwhelming that you can travel to/from the airport without incident, we aren’t enthusiastic about recommending the subway to Midway right now.

And unless you just absolutely need one, skip the rental car – it’s not worth it.

Now that you know how to get there, where should you stay? Check out the next part of The Stadium Insiders’ guide to Wrigley Field for all of the answers!