CHICAGO — On Wednesday, August 5, the Dodgers and Cubs throw out a 1:20 first pitch at Wrigley Field. Six and a half hours later and nine miles due south, the Sparks and the Sky tip off at Wintrust Arena.
Nobody planned that. It just happened. And it means that for the price of one train fare, you can watch a National League heavyweight fight in the sunshine, eat dumplings in Chinatown, and be inside a sold-out WNBA building before the sun goes down.
That Wednesday closes a three-game series that would be worth the flight by itself. Los Angeles and Chicago do not meet often, the bleachers will be a genuine split, and Wrigley in August has a particular kind of noise to it. So whether you are flying in from LAX or you have lived off the Red Line your whole life, this is the week to do it properly. Here is the full playbook.
- Monday, August 3: Dodgers at Cubs, 7:05 p.m. CT, Wrigley Field
- Tuesday, August 4: Dodgers at Cubs, 7:05 p.m. CT, Wrigley Field
Wednesday, August 5: Dodgers at Cubs, 1:20 p.m. CT, Wrigley Field
Wednesday, August 5: Sparks at Sky, 8:00 p.m. CT, Wintrust Arena
Monday, August 3: Dodgers at Cubs, 7:05 p.m. CT, Wrigley Field
Tuesday, August 4: Dodgers at Cubs, 7:05 p.m. CT, Wrigley Field
Wednesday, August 5: Dodgers at Cubs, 1:20 p.m. CT, Wrigley Field
Wednesday, August 5: Sparks at Sky, 8:00 p.m. CT, Wintrust Arena
If baseball is the entire point of the trip, sleep in Wrigleyville. Hotel Zachary sits directly across Clark Street from the marquee, which means you can watch the crowd form from your window and be at the gate in ninety seconds. Mordecai, the bar downstairs, is a genuinely good cocktail room in a neighborhood not famous for them. You pay for the address, and on a Dodgers midweek you pay a lot. Cheaper in the same orbit are the smaller boutique properties along Clark and Diversey in Lakeview. You lose the view and keep the walk.
If you are doing the Wednesday double, stay in the South Loop instead. The Marriott Marquis Chicago sits at McCormick Place, a short walk from Wintrust and two blocks from a Green Line stop that runs straight up to Wrigley. After a night game you walk to your room instead of arguing with a surge price. That is the whole case, and it is a strong one. Just watch the McCormick Place convention calendar, because when a big show is in town those rates jump overnight. The arena keeps a list of walkable hotels if you want to compare.
And if you want to come home feeling like you actually saw the city, book The Robey in Wicker Park. It is farther from both venues and it is the version of this trip you will still be describing in October.
Wrigley is 112 years old and it has no interest in your comfort. That is the appeal, but it rewards people who know what they are doing.
Get there when the gates open, roughly two hours before first pitch. Batting practice with the bleachers half empty is one of the best free hours in American sports, and it is the only window where the Clark and Addison marquee photo does not involve a forty-person scrum. Gallagher Way, the free plaza next door, is where you tell your group to meet, because half of them will be late.
On seats: the bleachers are a party and, in an August day game, a sunburn factory. The 200 level on the infield buys you shade and the best value sightline in the park. The upper deck behind home plate frames the ivy, the hand-turned scoreboard and the skyline in one shot, which is the photo everyone actually wants. One warning that costs people three hours of neck strain every single homestand: parts of the old grandstand still have support posts, so check the seat map before you buy anything in the lower reserved sections.
Once you are in, look at the flags on top of the scoreboard. Blowing out toward Waveland means bring your slugging percentage. Blowing in off the lake means you are watching a pitchers duel and telling everyone you planned it that way. Order a Chicago dog with no ketchup, drink an Old Style, and stay for the seventh-inning stretch even if your team is losing. Afterward, Murphy’s Bleachers at Sheffield and Waveland is the classic, and Nisei Lounge is the oldest bar in Wrigleyville and the least interested in impressing anyone, which is exactly why you go.
Dodgers fans, one note. You will not be lonely out there. Wear the blue, be gracious about it, and the neighborhood will treat you fine.
The Bag Rule That Will Ruin Your Wednesday
This is the single most useful thing in this guide, so read it twice. The two buildings do not have the same bag policy, and they are not close. Wrigley allows most soft bags up to 16 by 16 by 8 inches but bans backpacks outright, clear ones included. Wintrust is far stricter: clear bags no larger than 12 by 6 by 12 inches, or non-clear purses no larger than 10 by 6 by 2.
Translation: The tote that sails through the gate at Clark and Addison at one o’clock will get you turned away at Cermak Road at seven, and there is no bag check at either venue to save you. Carry the small clear bag all day. Wintrust is also fully cashless, so leave the cash in the room and bring a card.
Wintrust Arena, the Best Seat You Are Not Buying
Wintrust holds 10,387 people, which means the worst seat in that building is closer to the floor than a decent seat in most NBA arenas. You can hear the coaching. You can hear the players talking to each other. If you have only ever watched the WNBA on television, this is the game that ruins television for you.
Get in when doors open, about an hour before tip, because the tunnel during warmups is the most accessible player sightline you will get anywhere on this trip. The Sky publish a full gameday guide worth two minutes of your time. And skip the McCormick Place lot, where prepaid spots run around forty dollars, in favor of the Green Line stop at Cermak-McCormick that drops you a block from the door for pocket change.
Then sit lower than you think you need to. The gap between a thirty-five dollar upper and a seventy dollar lower here is the gap between watching a game and being inside one, and there is almost nowhere else in professional sports where that upgrade is that cheap.
Sausage is the most popular pie option at Lou Malnati s.
Sausage is the most popular pie option at Lou Malnati s.
Start with Italian beef, which is not optional. Mr. Beef on Orleans is the one the television show made famous and it had earned the attention long before that. Al’s on Taylor Street is the original, where the standing-room ritual is half the meal. Portillo’s on Ontario is the tourist-proof version and there is no shame in it. Order it dipped, with hot giardiniera, and wear a shirt you do not love.
Then pick your pizza fight. Pequod’s on Clybourn makes the caramelized-crust pan pizza that converts deep dish skeptics, and if you only have one pizza meal in you, spend it there. Lou Malnati’s is the reliable classic. But the pie Chicagoans actually eat on a Tuesday night is tavern-style thin cut into squares, and Vito and Nick’s on the South Side is the shrine.
The move nobody tells visitors, though, is Chinatown. It is roughly eight minutes from Wintrust Arena, which makes it the perfect Wednesday dinner between the final out and the opening tip. Qing Xiang Yuan for dumplings, MingHin for dim sum, Triple Crown when you need a table at an hour when nothing else will seat you. Elsewhere: Manny’s Deli in the South Loop for a corned beef sandwich that holds you through four quarters, Big Star and Smoke Daddy at Hotel Zachary for the Wrigleyville pregame, and Superdawg out on Milwaukee Avenue if you have a car and a sense of history.
Here is the route that works. Eat something light in Lakeview around 11:15, because you have a long day and a bigger dinner coming. Take the Red Line to Addison and be through the gate by noon. First pitch at 1:20, final out somewhere around 4:15, and this is the important part: do not linger. Move.
Ride the Red Line south to Roosevelt, transfer to the Green Line, and go one stop to Cermak-McCormick. Give it forty-five minutes and you will have room to spare. Eat in Chinatown at 5:30, sit down, drink water, then walk into Wintrust at 7:00 for warmups. Tip is at 8:00, and you will be out around 10:15 with enough energy left for one South Loop nightcap.
Both buildings empty into a rideshare surge at the exact moment the rest of the city is trying to get home. On this particular Wednesday, the train is not just cheaper. It is the only version of the plan that holds together.
Visitors take photos around Cloud Gate, known as The Bean, in downtown Chicago.
Megan Smith/USA TODAY Network / USA TODAY NETWORK via Imagn Images
Visitors take photos around Cloud Gate, known as The Bean, in downtown Chicago.
You have two open mornings and one long afternoon, so do not waste them in a hotel gym. The Chicago Architecture Center river cruise is ninety minutes and the best possible introduction to this city, though it sells out in August so book ahead. Walk the Riverwalk at golden hour and cut up to Millennium Park for Cloud Gate, with the Art Institute right there and air conditioned when the heat wins.
The thing visitors never believe until they see it is that Chicago is a beach city in August. North Avenue Beach and Montrose Beach are real beaches with real skyline views, and Montrose is a straight shot from Wrigleyville. For a night off, the Green Mill in Uptown still plays jazz in a room that has barely changed since Prohibition. If you want the best free photograph in the city, walk fifteen minutes from Wintrust to the steps of the Adler Planetarium and turn around. And if you have a whole extra day, Choose Chicago keeps the most reliable calendar of what is happening in each neighborhood that week.
Four events in three days means four rounds of checkout fees, and that is where a trip like this quietly gets expensive. TickPick prices all in with no buyer fees, so the number on the seat map is the number that hits your card. Across a week like this, that difference is a dinner.
Two buying notes. Wrigley bleacher and upper deck prices climb as a Dodgers series gets close, so move early on those. And if you are flexible about which Cubs game you attend, the Wednesday day game is usually the softest of a three-game set. Grab all four games on TickPick before you book the hotel, because ticket prices move faster than room rates.
Is there really a Cubs game and a Sky game on the same day?
Yes. Wednesday, August 5 has a 1:20 p.m. CT first pitch at Wrigley Field and an 8:00 p.m. CT tip between the Sparks and the Sky at Wintrust Arena. Both are comfortably doable with public transit and a dinner in between.
How far is Wintrust Arena from Wrigley Field?
About nine miles by road. Plan on forty to fifty minutes using the Red Line and Green Line, and considerably longer by car in evening traffic.
Can I bring the same bag to both venues?
Probably not. Wrigley permits soft bags up to 16 by 16 by 8 inches but no backpacks, while Wintrust caps clear bags at 12 by 6 by 12 inches and non-clear bags at 10 by 6 by 2. Carry the smaller clear bag and you are fine at both.
Do I need a car in Chicago for this trip?
No. Both venues sit within a block of a train station, and parking around Wrigley is expensive and slow. Take the train.
What is the best neighborhood to stay in?
South Loop if you are attending both the Cubs and the Sky, because Wintrust is walkable and Wrigley is a direct ride. Wrigleyville if baseball is the entire trip.
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