Roaring Twenties <strong>Chicago</strong>

Roaring Twenties Chicago

Illinois - Illinois

Take a Lindy Hop back in time on our Roaring Twenties road trip of Chicago’s most iconic sights. Experience the razzle-dazzle of the historic theater district, trace the footsteps of bootleggers, and grab a deep-dish pizza or two along the way.

Hit the open road and explore Starved Rock State Park, before returning to Downtown to enjoy your new-found freedom at one of the city’s coolest jazz clubs.

Neon lights, Ferris wheels, and all-American diners – enjoy all this and more on your roaring Chicago road trip.

What to drive:

Make the most of your US road trip with something from our American Collection:

Ford Mustang GT coupe

Ford Mustang GT coupe

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Chevrolet Camaro SS convertible

Chevrolet Camaro SS convertible

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Route 66

Roaring Twenties Chicago

Stop 1: Route 66 1/14

Kick start your trip on Route 66 – one of the world’s most iconic roads.

Once known as the ‘Main Street of America’, this historic highway was constructed in 1926, running from Chicago to Los Angeles. Lined with classic diners, cafes, motels, and tourist attractions, it inspired the original American road trip.

You’ll find the iconic ‘Begin’ sign just outside the Art Institute of Chicago in Downtown – take a snap before you start your Windy City adventure. You can also find out more about exploring Route 66 in our Getting Your Kicks road trip.

78-98 E Adams St, Chicago, IL 60603

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The Chicago Theatre

Roaring Twenties Chicago

Stop 2: The Chicago Theatre 2/14

Entertaining crowds since 1921, the Chicago Theater has stood the test of time and its flashing neon sign has become an unofficial emblem of the city.

Bringing live jazz and early motion pictures to Chicago under the Balaban and Katz theater chain, today it showcases award-winning stage shows and concerts.

Enjoy a tour of the theater’s French Baroque grand lobby and take a bow on the legendary stage. While wandering the halls, admire the dressing room walls, signed by famous artists who have performed here – from Dean Martin to Dolly Parton.

175 N State St, Chicago, IL 60601

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Chicago Riverwalk

Roaring Twenties Chicago

Stop 3: Chicago Riverwalk 3/14

Immerse yourself in Chi-Town’s vibrant atmosphere with a stroll along the iconic Lake Michigan waterfront. The 1.25-mile route features six coves, each with a distinct personality.

Head to the Marina to enjoy al fresco dining along the river. The Boardwalk also offers picturesque views of the three branches of the Chicago River, while the Jetty is the perfect place to bird-watch or try your hand at fishing.

Stroll at your own pace and enjoy live music and a trail of public artwork dotted along the walkways, including Art on theMART – the world’s largest permanent digital art installation.

Chicago, IL 60601

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Willis Tower

Roaring Twenties Chicago

Stop 4: Willis Tower 4/14

As Chicago’s tallest skyscraper – and the third tallest building in the US – Willis Tower offers unparalleled views from its Skydeck. Travel 1,353 feet up to the 103rd floor and step onto The Ledge. This glass-bottom observation deck extends from the building, where you can take a seat above the city’s skyline for an unforgettable photo op.

Gaze down onto the bustling city below and, on a clear day, enjoy 50-mile views out to Indiana, Wisconsin, and Michigan.

233 S Wacker Dr, Chicago, IL 60606

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Lou Mitchell’s

Roaring Twenties Chicago

Stop 5: Lou Mitchell’s 5/14

Who said breakfast should only be eaten in the morning? Lou Mitchell’s has been flipping pancakes and serving all-day breakfasts since 1923.

This historic American diner was the first restaurant stop on the original Route 66, and has been a favorite with locals and tourists ever since. Drop by for a fresh cup of coffee, choose from more than 20 kinds of omelet, savor delectable donut holes, or enjoy a classic vanilla shake before hitting the road.

565 W Jackson Blvd, Chicago, IL 60661

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Ambler’s Texaco Station

Roaring Twenties Chicago

Stop 6: Ambler’s Texaco Station 6/14

From the white cottage-style building to the tall red pumps, gas stations don’t get more Americana than Ambler’s Texaco Station. Between 1933 and 1999, it fueled travelers driving along Route 66 for, coincidentally, 66 years. It’s now restored and is on the National Register of Historic Places.

While you can’t fill up your tank anymore, you can fill up on history. Venture inside and explore the museum filled with Route 66 memorabilia including road signs, maps, original gas pumps, and even a 1914 Model-T Ford.

W Waupansie St, Dwight, IL 60420

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Starved Rock State Park

Roaring Twenties Chicago

Stop 7: Starved Rock State Park 7/14

Rekindle the new-found freedom of the 1920s with an escape to the mountains and discover the sandstone canyons and lush parklands of Starved Rock State Park.

Situated on the Illinois River bluff, you can tackle 13 miles of hiking trails through the park’s 18 canyons. Step into a world of towering trees, cascading waterfalls, and a cornucopia of native wildlife – from bald eagles to raccoons and coyotes.

Remember to pack a picnic lunch for the family or experience fine dining at Starved Rock Lodge – an authentic stone and log-built lodge dating back to 1933

2678 E 875th Rd, Oglesby, IL 61348

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Coronado Performing Arts Center

Roaring Twenties Chicago

Stop 8: Coronado Performing Arts Center 8/14

While traveling along I-39, break up your journey back to Chicago with a stop at Rockford’s beautiful 1927 theater. From the Marx Brothers to Frank Sinatra, this historic stage has welcomed countless legendary performers.

The majestic auditorium is reminiscent of the movie palaces of the 1920s. Gilded facades of Spanish castles and Italian villas line the walls, while the star-dotted ceiling glistens above.

Settle into the plush red seats on the main floor or head to a balcony and catch one of the latest stage shows.

314 N Main St, Rockford, IL 61101

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Superdawg Drive-In

Roaring Twenties Chicago

Stop 9: Superdawg Drive-In 9/14

As you enter the North Side of Chicago, look out for the distinctive neon sign and two giant fiberglass hot dogs standing atop Chicago’s only drive-in restaurant.

Located on the same site as the original Superdawg stand, not much has changed since 1948 – from the family owners, to the hot dog recipe.

Chow down on a pure beef hot dog, with all the tangy trimmings, including mustard, piccalilli, and a dash of spicy hot pepper sauce. Pair it with their signature crinkle-cut Superfries and a Supermalt for the true Superdawg experience.

6363 N Milwaukee Ave, Chicago, IL 60646

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Wrigley Field

Roaring Twenties Chicago

Stop 10: Wrigley Field 10/14

You can’t visit Chicago’s North Side without stopping by Wrigley Field – the home of the Chicago Cubs baseball team since 1916. Put on your best blue shirt and join the electric crowds to cheer on the Cubs at a ball game.

If you happen to visit during offseason, take a tour of the stadium and listen to stories about the Major League’s second-oldest ballpark. You can even step into the dugout where Chicago Cubs’ legends once sat, including Ron Santo and Ernie Banks. Don’t forget to pick up a souvenir at one of the merchandise stores – from flags and mugs to your very own Wrigley Field T-shirt.

1060 W Addison St, Chicago, IL 60613

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Chicago Pizza and Oven Grinder

Roaring Twenties Chicago

Stop 11: Chicago Pizza and Oven Grinder 11/14

It wasn’t all glitz and glamor in the 1920s, and the Chicago Pizza and Oven Grinder tells part of the city’s infamous, not to mention gruelling, history. The restaurant is opposite the site of the notorious St Valentine’s Day Massacre of 1929, ordered by crime boss Al Capone and is even rumored to have been a lookout post.

Today, you’ll be relieved to hear that things have calmed down significantly. Stop by and pick up a signature Pizza Pot Pie, or order a classic Italian sub for an authentic taste of Chicago.

2121 N Clark St, Chicago, IL 60614

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Magnificent Mile

Roaring Twenties Chicago

Stop 12: Magnificent Mile 12/14

North Michigan Avenue is one of today's 20s' most vibrant streets. Park up and explore more than 460 retailers, ranging from upscale department stores to luxury retail outlets. While exploring, you’ll find the Wrigley Building, a classic example of 1920s architecture, and the iconic Tribune Tower.

The Magnificent Mile is also a great stop for foodies, with 275 restaurants to choose from. For a taste of Chicago history, check out Uno Pizzeria – the original creators of the city’s iconic deep-dish pizza.

Chicago, IL 60611

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Navy Pier

Roaring Twenties Chicago

Stop 13: Navy Pier 13/14

Chicago’s waterfront treasure along the shores of Lake Michigan has been entertaining millions of visitors since its opening in 1916. Watch the world go by while you relax on the famous Centennial Wheel or take a ride on the 1920s-inspired carousel.

Visit the Chicago Children’s Museum, where kids can dig for dinosaur bones and splash about in the water playground. The Pier offers year-round fun for all ages, with fireworks displays, live music, Shakespeare Theater, and amazing cruises.

600 E Grand Ave, Chicago, IL 60611

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Andy’s Jazz Club

Roaring Twenties Chicago

Stop 14: Andy’s Jazz Club 14/14

We finish our road trip in one of Chicago’s coolest venues: Andy’s Jazz Club. And yes, we’re cheating a little – it wasn’t founded until 1950 – but it embodies so much of the musical freedom the Roaring Twenties were known for.

Head on down for Jazz at Five to check out the city’s top local performers. While you’re there, tuck into a casual dinner as you listen to the variety of music on offer, from Traditional and Swing, to Fusion and Bop.

11 E Hubbard St, Chicago, IL 60611

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