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Why Chicagoans Shouldn’t Sleep on Route 66

Published Nov 11, 2024

In Partnership With 

City Cast Chicago

Written by 

OnlyInYourState Staff

City Cast Chicago is the easiest way to stay updated on what's happening in Chicago. Their daily podcast and newsletter covers local news, gives the best life hacks, and curates recommended events. For more Chicago insider information visit chicago.citycast.fm.

Street view featuring a "Historic Route 66" sign, with buildings and banners in a bustling urban setting.
Route 66 begins in downtown Chicago. (Hugo Magalhaes / Pexels)

Route 66, arguably the most famous highway in America, has a start and end point in Chicago. But the Mother Road isn’t as big of a deal here as it is in other towns along the 2,448-mile highway. Tour guide Mike McMains says that’s because Chicago just has a lot of stuff going on.

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But in collaboration with the state and city ahead of the route’s centennial in 2026, McMains’ new trolley tour is showing locals notable spots along the Chicago leg of the route, which stretches west from downtown.

A group of people on a trolley, smiling and holding drinks, enjoying a fun outing together.
Shots from Mike McMains’ Route 66 tour — including a surprise run-in with historian Shermann “Dilla” Thomas. (Courtesy of Mike McMains)

Something to Eat

You can get jerk spices from Jerky Jerk, sandwiches and pasta from Ferrara Bakery, and hot dogs from Lulu’s all on Taylor Street. Lou Mitchell’s is older than the highway itself. La Catedral, which has locations in Little Village and North Lawndale, touts itself as home to the world’s best chilaquiles.

Something to See

Visit where Martin Luther King Jr.’s West Side apartment once stood. The civil rights activist lived in the city in the late '60s to protest unfair housing practices. Then, check out an antique car show outside of La Catedral in North Lawndale Saturday and Sunday. Anyone can catch it — not just folks on the tour.

Something to Do

The Epiphany Center for the Arts is a former church and Black Panther gathering spot that has been turned into an arts center with exhibits and concerts. Pop into the Art Institute for a self-guided tour of items from Route 66 states.

Map of the Chicago area highlighting major highways, towns, and landmarks, including Route 66 and various restaurants.
The Chicagoland section of Route 66. (U.S. Department of Transportation)

The last weekend of tours is here. Check online to see if tickets are available. Alternatively, you can wait in the bus loading zone and claim a no-show ticket.

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Don’t sleep on McMains’ other unique tours from Chicago’s ugly buildings to underground rats. He has an upcoming Illinois presidents tour ahead of the Democratic National Convention and election.

Check out more Chicago insider information with City Cast Chicago. Their daily newsletter and podcast are the easiest way to stay up-to-date on Chicago. For life hacks, daily event recommendations, and local news visit chicago.citycast.fm.

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Experiences

Walk a Mile on Lincoln Avenue

Published Nov 11, 2024

In Partnership With 

City Cast Chicago

Written by 

OnlyInYourState Staff

City Cast Chicago is the easiest way to stay updated on what's happening in Chicago. Their daily podcast and newsletter covers local news, gives the best life hacks, and curates recommended events. For more Chicago insider information visit chicago.citycast.fm.

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A person takes a selfie by a fountain, holding a drink, with a text message overlay inviting a walk on Lincoln Ave.

Another week, another walking series! This time, I walked a stretch of Lincoln Avenue in Lincoln Square.

How it Works

  1. 1.
    We pick a street within city limits.
  2. 2.
    We pick a mile on that street (Lincoln Avenue between Lawrence and Warner avenues)
  3. 3.
    We recommend ~10 things to do in that mile.
Map showing a section of N Western Ave with various points of interest and streets, including Welles Park and Hop Butcher.
A few stops along Lincoln Avenue. (Google Maps)

How to Get There

  • The Brown Line at Western Avenue
  • No. 81 bus to Western Avenue
  • No. 50 or 49 bus to Lawrence Avenue
  • Divvy at Western and Leland avenues or Lincoln and Sunnyside avenues

What to Do

First, let’s fuel up: Gene’s Sausage Shop has beer, bratwurst, and rooftop views, and Luella’s Southern Kitchen has the flakiest biscuits in town.

Once you’re fueled up, pop over to Merz Apothecary for the skincare and soaps of your dreams. If you have a little one, Timeless Toys has games, trinkets, and more.

Ready for entertainment? Laurie’s Planet of Sound has a particularly good indie- and alt-rock selection. The Davis Theater is showing new films like “Beetlejuice Beetlejuice” and old releases like “Whiplash.”

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The Old Town School of Folk Music has classes for Chicagoans who want to learn guitar, dance, and more. The music school also hosts great — and sometimes free — concerts.

Archway sign reading "Lincoln Square" against a clear blue sky, with buildings and trees in the background.
In one mile, you can stop at Gene’s Sausage Shop, Timeless Toys, Luella’s, the Davis Theater, and Welles Park. (Sidney Madden / City Cast Chicago)

In one mile, you can stop at Gene’s Sausage Shop, Timeless Toys, Luella’s, the Davis Theater, and Welles Park. (Sidney Madden / City Cast Chicago)

If you’re looking for a place to study, co-work, or just bask in the natural light, head to Sulzer Regional Library. When you’re ready for fresh air, head across the street to Welles Park for family fun and fitness.

Walk further down to the Cornservatory Theatre for comedy shows. This week, the run of “We Should Kill Him” ends, but “Yes Chef!” opens!

Don’t just take in art: Make art at the Lincoln Square Pottery Studio! Students can learn how to use the wheel or hand-build. But secure your spot fast — classes sell out.

Anyone got a walking playlist? City Casters are putting in the miles 🥵

Check out more Chicago insider information with City Cast Chicago. Their daily newsletter and podcast are the easiest way to stay up-to-date on Chicago. For life hacks, daily event recommendations, and local news visit chicago.citycast.fm.

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Experiences

Ride a Christmas Train, Then Stay at a Decked-for-Christmas Hotel for a Holly Jolly Illinois Adventure

Experience a festive holiday train ride at the Illinois Railway Museum and enjoy holiday decor at the Embassy Suites Riverfront in Rockford.

Updated Oct 23, 2024

Written by 

Trent Jonas

The holidays in Illinois are a special time of year. Every corner of our state embraces the season, from the small towns to the bigger cities and just about everywhere in between. This holiday season, hop aboard for an Illinois Christmas train adventure at the Happy Holiday Railway - a beloved annual event hosted by the Illinois Railway Museum. Then fully embrace the holiday spirit at the Embassy Suites Riverfront in Rockford, where the halls are decked and good tidings await.

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Snow-covered railway tracks stretch into the distance, flanked by gravel and a snowy landscape.
Train Tracks and Railroad Ties in winter Landscape

Begin your adventure by making your way to the Illinois Railway Museum's depot to get your tickets for your ride on the Happy Holiday Railway. You can purchase tickets in advance, as well. Cookies and hot chocolate are available while you wait to board, and the museum is completely decked out for the occasion! The train runs on most Saturdays and Sundays during the holiday season. Rides are scheduled for 11:30 am, 12:30 pm, 1:30 pm, 2:30 pm, 4:00 pm, 5:00 pm, and 6:00 pm. Tickets are $25, with ages two and under riding for free. You'll want to arrive approximately 30 minutes before your departure time.

The Happy Holiday Railway rides last about 40 minutes, but you'll feel as if you've been transported into a magical holiday world. You may even run into one very special conductor's helper. (Actually, he rides along on every train!)

A Santa figure entertains children on a decorated train, with colorful lights and excited expressions.
Kevin Brown / Flickr

After your Christmas train adventure, chug on over to the Embassy Suites Riverfront in nearby Rockford, which is at the very center of all of Rockford's holiday festivities. And with the way the hotel gets decked out, you can tell it takes its role very seriously. Enjoy all of the hotel's uplifting holiday decor. Boost your own spirits with a seasonal cocktail -- or hot cocoa -- at The Top, the hotel's aptly named rooftop bar and lounge.

While you're sipping a cup of cheer, you'll enjoy views out over the river and Davis Park, which is always festively lighted for the holidays.

A person's hands holding a cup of hot chocolate, viewed from above, with a frothy surface.
This image captures the essence of winter comfort, with a close-up of two hands gently cradling a cup of hot chocolate. The frothy beverage is in sharp focus, highlighting its rich texture and inviting warmth against a blurred outdoor backdrop, suggesting a chilly but cozy atmosphere

Head to the Illinois Railway Museum online for times, dates, tickets, and more. And be sure to visit the Embassy Suites Rockford's Facebook page to see what the hotel has in store for this holiday season.

Have you boarded the Happy Holiday Railway or had a chance to discover why Rockford is the most festive Christmas town in Illinois? And speaking of Christmas in Illinois, be sure to take a look at our ultimate gift-giving guide for all the travel enthusiasts on your list this year.

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