Drive the Coast Into Chicago

Enjoy complimentary breakfast at your hotel and check out before continuing your route from Michigan City to Chicago.

Before heading out of Indiana, visit the Century of Progress Homes that line the coast of the Beverly Shores within the park. The homes were originally built as part of Chicago's 1933 World Fair, which sought to celebrate futuristic changes and innovations in architecture, science, and technology. The "Homes of Tomorrow" houses hoped to offer what the future of residential structures and home furnishings could look like—they're so futuristic that some still look modern today.
Now, five of the homes from the World Fair sit on the Indiana Dunes National Lakeshore, and four of them have been restored and occupied. Visitors cannot tour the inside because of this, but with respect, the houses can be viewed outside, and there are informational plaques offering information about each house.

Heading up into Chicago, stop off at Rainbow Beach Park, a public beach situated just south of Chicago that boasts expansive views of Chicago's skyline. Photographers flock to this location for the sea and city skyline views—it's a view you don't want to miss.

When arriving in Chicago, stop in at your hotel to have your car parked with an onsite valet and check in to the hotel. The Pendry is a boutique luxury hotel that sits within the historic 1929 Art Deco Carbide & Carbon Building. There is a fitness and wellness center, bar, rooftop bar, and French restaurant within the hotel.

From your hotel, walk across the DuSable Bridge and catch the first sights of the Chicago Riverwalk before digging into one of Chicago's famed deep-dish pizza institutions, Lou Malnati's. Lou's is famous for its buttery, flaky crust and gooey deep dish slices. Lou's has been around the block since the inception of Chicago-style pizza and is an argued favorite among locals and visitors alike.

One of the best ways to learn about Chicago's history and see the city is through their architecture river cruises. The cruises bring you on a guided journey on Chicago's historic river, covering over 40 different important buildings in Chicago's history like the John Hancock Building and the Willis Tower. You'll hear live commentary from an expert while appreciating the stunning skyline views.
Book here

Walk back over toward the Millenium Park neighborhood for happy hour drinks at Cindy’s rooftop, which offers stunning overlooks of Millennium Park and the famous silver Bean, The Art Institute of Chicago, downtown Chicago, and the Chicago River. Make reservations in advance to ensure you can snag a spot—this place is popular for its stylish atmosphere and gorgeous views, craft cocktails, and sits atop the Chicago Athletic Association.
Reservations are required for dinner, but not necessary if just stopping in for drinks, though availability is a first-come, first-serve basis, so it's good to arrive early before the dinner rush.

After some rooftop views and drinks, walk downstairs to see the Cloud Gate, aka "The Bean," up close, a famous public art sculpture built by artist Anish Kapoor that millions capture photos of every year. The sculpture reflects the activities of the park and the vast skyline back to viewers, asking them to observe, touch, and interact with their surroundings and the sculpture's liquid-like surface.

Take the Green Line over to Time Out Market for a sampling of the best food Chicago has to offer. This rotating, curated marketplace offers 18 restaurants, three bars, a demo kitchen, and a rooftop terrace. This is a great option to eat at as a visitor as you get a selection of some of the best Chicago eateries all in one place.

If you are up for it, experience a taste of Chicago's vast theater and entertainment scene by catching one of the funniest late-night comedy shows in the world at Chicago's legendary club, The Second City. This location launched the careers of late-night comedy legends such as Tina Fey, Amy Poehler, Bill Murray, Steve Carell, and many others.
Buy tickets directly on their website.

Hail a taxi or call a cab before settling back in for the night at the hotel for a quiet and comfortable night's rest. You can have breakfast directly in the hotel if you'd like before heading out for the day.