The city of Chicago has two baseball teams, a football team and 10 million residents. The Chicago metropolitan area also has a number of casinos in the downtown area by the lakefront.

Horseshoe Hammond Casino

The Horseshoe Hammond Casino is located 17 miles from downtown Chicago so why not end up here after a long scenic waterside run?

It’s the busiest casino within the Chicago city limits. Set within the marina, the property includes 108,000 square feet of casino space, on par with many of the mega resorts in Las Vegas.

The casino has thousands of slot machines and video poker machines and over 100 table games. These include all the favorites such as blackjack, craps, roulette and baccarat.

It also has the area’s largest poker room which comprises 34 tables. Many big tournaments are held here including the World Series of Poker circuit events.

As sports betting is now legal in Indiana the casino also caters for fans of a number of sportsbooks. The Horseshoe Hammond is also home to a large concert venue and 4 restaurants.

The Horseshoe is owned by Caesars Entertainment which means you can use your Caesars Rewards Card here. There are numerous free shuttles running to and from downtown Chicago so you won’t have to run back!

Ameristar East Chicago

The Ameristar is the closest casino to Chicago with a hotel. As it’s located almost 24 miles from downtown Chicago that could come in handy if you don’t fancy making the journey back after a long run. Like the Horseshoe it is in a marina. In addition to its 288 hotel rooms and 6 restaurants the Ameristar has over fifty thousand square feet of casino floor space. This incorporates 1,700 slot machines and 65 table games. It also has a sportsbook with 12 betting kiosks.

Rivers Casino

The Rivers casino is located near the airport but if you´re running out from the city you can take a route that goes through beautiful scenery. Take a route that goes via the Acacia Park cemetery, Schiller Woods and the Forest preserves of Cook County. The casino has more slots than any other in Illinois and claims to have the biggest payouts on table games. With plenty of accomodation and restaurant options this is a perfect location to finish your casino run

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Polar Dash Half Marathon

If you can deal with the icy temperatures this race is highly recommended. Athletes can compete in half marathons, 10Ks, 5Ks or 1,700 metre runs alongisde Chicago’s Lakefront Trail. You´ll move from Soldier Field through various parks and back, to finish up.

Race to Wrigley 5K

If you’re a Chicago Cubs fan, this 5K, open to all age groups, is a great way to see Wrigley Field. The course starts and ends at the stadium and winds its way through Lakeview neighborhood. Not only that but your entry fee helps go towards Cubs charities. These help to increase access to sports and fitness for at risk individuals. If you´re one of the first hundred people to raise $500 you also receive a baseball signed by the players.

Hot Chocolate 15K/5K

Whatever your age or ability, this race is one of the first in the winter calendar. Both races start and finish in Grant Park and are lined with “sweet stations” handing out marshmallows and chocolate chips. At the finish you´ll also be handed a finisher’s mug filled with other treats. You’ll also receive a finisher’s jacket. One of the best races in Chicago!

Soldier Field 10 Mile

For fans of both football and running, this race takes in a few sites of interest. You’ll start in Soldier Field, home of the Chicago Bears, and then take a mostly rural route along the Lake Shore Drive. After that you´ll head back to Soldier Field to finish in the stadium. Stick around for the post-race party with live music and free beer from local craft brewery Goose Island.

Bank of America Shamrock Shuffle

Whilst it doesn’t actually take place on St. Patrick’s Day itself you are still encouraged to dress up in your favourite green outfit. The 8K race winds through downtown and ends up in Grant Park where you can celebrate finishing with beer and music. The fun continues at a local restaurant if you want to carry on the party.

Chicago Half Marathon & 5K

The Chicago Half Marathon is a very popular race in Chicago. Thanks in part to its home stretch which is the traffic-free Lake Shore Drive. Take in the beautiful and unobstructed views of the skyline and Lake Michigan as you head to the finish by the golden Statue of the Republic. Starting the race in Jackson Park you´ll run through the University of Chicago campus and Hyde Park neighborhood.

Rock ‘n’ Roll Chicago Half Marathon

The Rock ‘n’ Roll Half Marathon in Chicago is essentially a party you run. The streets are lined with cheering spectators and local bands who provide you with your race soundtrack. You´ll head through downtown, crossing the Chicago River and the Theatre District. When you finally reach the finish line, carry on the party at the festival and concert you´re greeted with.

Chicago Triathlon

This is the city’s only swim-bike-run event. During the weekend there are five different triathlons. For the adults there are the Olympic, Sprint and Supersprint races while kids have two separate races. The race incorporates a swim in the harbor, a ride through the city , and finally a run along Lake Shore Drive finishing up in Grant Park!

Chicago Marathon

Athletes come from both all over the US and all over the world to participate in this major event. Not only one of the best races in Chicago it is one of the best in the world. Its popularity means it can regularly attract over 1.75 million spectators. Due its flat, fast course many records have been broken over the years. The course passes through both central tourist areas and 29 unique neighborhoods. You can also expect to get free beer and massages at the finish line.

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Its history goes back to 1905 when just 15 athletes participated. Only 7 of those actually finished the race. Nowadays around 45,000 people run the event including many world class athletes. Known for its flat and fast course it winds through one of the world’s most scenic city centres. It has produced four world records, a number of national records and many personal bests.

Runners can expect up to 1.7 million spectators lining the streets as they run through the 29 neighborhoods.

Last year however saw some changes as a result of the pandemic. The race was run virtually to stop crowds gathering and avoid spreading the virus. Registered runners had the choice of deferring to next year’s race or competing as a part of a virtual community. These were via self-designed courses throughout Chicago.

Running groups from the city organised to provide hydration stations along the Lakefront Trail route. The largest organisation, CARA also provided stations in five different suburban locations. CARA usually has about 2,000 runners doing the marathon but only 700 members participated in the virtual event.

Whilst disappointed a lot of the group were excited to help out also handing out oranges, running gel and vaseline.

Many runners headed to the lake, forests or their neighborhood streets to run their routes but were sad to miss out on the traditional sights and sounds that runners encounter every year. These include the colorful parties in Lakeview East, the dancing dragons in Chinatown and the bridges across the Chicago River.

Another thing missing was the absence of cheering spectators lining the sidewalks. An exciting and energy boosting experience for both athlete and spectator alike.

This year’s event will also be very different and will be unlikely to draw many of the world’s best runners. Competition to sign them up is particularly fierce. This is due to the other major marathons all having to fit their races into the same 2 month window in the fall.

The Boston Marathon is usually held in April but this year falls on October 11th, the day after the Chicago marathon. For that reason this year more emphasis will be placed on giving opportunities to athletes who haven’t had an opportunity within the last couple of years.

Many top athletes are expected to compete.

A lot of them run one marathon within the spring and one within the fall. For that reason they have to decide in advance which races they’ll run. The organisers are still holding out for some big names however and talks are underway with managers and coaches.

The reality is though that it won’t be anything like the huge events of previous years. Despite this, all efforts are being made to make it as good as possible given the limitations. With vaccinations taking place across the country there is optimism that things could be back to normal by next year.

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Chicago Area Runner’s Association (CARA)
This club has been literally running for over 40 years. They offer group training programs, discounts on races and organise team and individual competitions for locals. Visitors can meet at weekly 5K and 1-mile events located in parks all around the city. The events run all summer and fall. You can participate in Six Series races: 3 or 5 mile Tuesday-night fun runs that meet at different bar every week.

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This hip social media-savvy crew take over the streets in and around Logan Square on Tuesday mornings and Thursday nights. Other events they have started include a run in University Village on Tuesday nights and a Saturday morning meet up in different locations. New visitors are warmly welcomed and the group´s signature black and white singlets are popular sellers. One of the coolest running clubs in Chicago

Weather Mark Running Club
This group holds runs every Tuesday at 6:15. You can drop off your stuff first at the Weather Mark Tavern in the city’s South Loop, close to the marathon course and head to the lakefront for a 5K run. We suggest joining your fellow runners back at the bar for a beer and food.

Chicago Area Runners Association

This is the original big running club in Chicago who recently celebrated their 40th anniversary. They have in excess of 9000 members and all ages and abilities are welcome. Training programs for marathon runners are run alongside beginners courses that train people for their first 5k. The CARA Stars youth group is a popular choice for budding runners between 6 and 15.

Universal Sole

Universal Sole operated as a running store for 20 years before closing in 2017. Since then it has focused on a more events based business. Events they host include monthly Tap Room runs visiting various renowned craft beer establishments across the city. Other events include trail runs and a Burger and Beer 5K run.

Chicago Endurance Sports

A common site by the lakefront on Saturday mornings is this friendly group that run events during Summer and Fall. they are a running club in Chicago group that welcomes runners of all abilities but especially help those looking to complete their first half or full marathon.

Hash House Harriers

A free to join club but members donate $6 every run for post run refreshments. With the motto “a drinking club with a running problem” this club is perfect for those who like to wind down with a beer after a jog. They typically run every Monday and Thursday night.

Fleet Feet Sports

This local retail chain organises three to six mile runs. It tends to attract suburban locals looking to fit in a run before travelling to work. They also offer membership to the Fleet Feet Nike Racing Team for $85 which provides coaching and a uniform. ($85). The runs start outside each six shop locations at 6:30pm each Monday. They also organise ladies only races.

Frontrunners/Frontwalkers

This running club caters for all ages and backgrounds but most of the 250 members of this running club are LGBTQ. They get together twice a week for a one or two mile walk or a three to five mile run. The group also organises social events like picnics and a Labor Day get-together with other Midwest chapters. They meet by the totem pole at Addison Street on Saturdays at 9am and Tuesdays at 6.30pm.

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Chicago Lakefront Trail

Possibly the finest running route in all of Chicago, this 18-mile path stretches alongside the lake shoreline. It offers plenty of places to stop off including restrooms and water stops. There are also many beautiful landmarks to see such as Soldier Field, North Avenue Beach and Navy Pier along the way. Back in 1836 the aim was to make this a public ground forever. For that reason there are no buildings or obstacles blocking the views. In 2017 plans were started to create separate lanes for pedestrians and cyclists to avoid accidents.

The 606, or Bloomingdale Trail

This route was once a railway line which served the thriving manufacturing district. These days this 2.7-mile elevated trail connects the western Chicago neighborhoods of Wicker Park, Humboldt Park, Bucktown, and Logan Square. Start your run at the easternmost point in Ashland Avenue. and Marshfield Avenue. and head west until you reach the Ridgeway Trailhead. The Exelon Observatory hosts monthly events for stargazers here. Also watch out for all the artwork along the route. These include murals and sculptures like Brick House, which resembles an enormous snake made entirely from tires and steel.

North Branch Trail

During busy times like summer or a fall day when the lakefront’s full of marathon-training groups, be sure to head northwest for a change of scenery. You can park up at any one of the lots here and then follow this shady, mostly flat route through wooded areas. The route ends up in Glencoe and the beautiful Chicago Botanic Garden. If at you feel tired at any point, hire a $7/hour bike rental and cycle back.

Waterfall Glen Forest Preserve

For those runners looking for more of a challenge than the other easier flat routes, head out of town to this spot. Nicknamed Big Bertha, this is a 9.5-mile loop in Darien, a 25-mile drive from downtown Chicago. A trail race is also held here each Summer called the Waterfall Glen Xtreme 10.

Grant Park

This park was modeled after the gardens at Versailles and runs between Michigan Avenue and the Museum Campus. It´s quite a sensation to run through these trees and paths and is a change in scenery from the Lakefront Trail. Highlights along the way the Buckingham Fountain as well as other sculptures and monuments. The northwest section of the park houses Millennium Park and the Art Institute of Chicago. A loop including the main paths of Grant Park is approximately 3 miles. Running the perimeter of Millennium Park will add another mile.

The Loop

This run includes a number of Chicago’s most impressive buildings. It should be said that this route isn’t really designed for running and there aren’t any designated running paths. For amateurs looking for a scenic jog however this is a fantastic route and one of the best running routes in Chicago. The best time to do it is first thing in the morning or in the evening to avoid the crowds.

North Shore

There are some great routes in this part of the city. These include some beautiful parks and residential neighborhoods. One route follows the North Shore Classic Half Marathon course which incorporates the Highland Park neighborhood. Your run will take in a number of classic, tree-lined streets made famous in movies. Many of these are John Hughes productions such as Ferris Bueller’s Day Off, Sixteen Candles and The Breakfast Club. The loop follows a counter-clockwise loop of the North Shore area.

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