Midwest · A day worth getting out for.

Out of Chicago.
Onto the open road.

Hike the canyons of Starved Rock, climb the 3 Dune Challenge at Indiana Dunes, cruise Lake Geneva past its lakeside mansions, walk Galena’s Main Street and Grant’s home, or follow Route 66 from its Begin sign to Pontiac. We’ve put the stops, routes and practical details together so your day out of Chicago is easier to plan.

Find your next day out
Every guide $4One purchase. Yours for good.No subscription
A wide, empty sand beach curving along Lake Michigan under a blue sky, with white-capped waves on the right and a wooded dune in orange and red fall color rising on the left
THE MIDWEST COLLECTIONCanyons. Dunes. Lake towns.Indiana Dunes, Indiana
GREAT
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✓ No ads. No pop-ups.✓ A day that actually fits✓ Routes ready for your phone✓ Rules, fees & things to watch for✓ A weather backup plan✓ Best-time advice for every trip
Small price. A whole day of possibilities.

Where will your Midwest day take you?

From Lake Michigan’s dunes to the Mississippi bluffs.
Every guide is $4.
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The wide Illinois River curving past a long wooded bluff in red, orange and gold fall color, with dark green pines at the water's edge and two small motorboats leaving wakesCanyon hiking & state parks
Chicago → Starved Rock → French & Wildcat canyons → Starved Rock Lodge → St. Louis Canyon → Illinois Waterway Visitor Center → Matthiessen Dells → Utica

Starved Rock & Matthiessen

A canyon-hiking day trip from downtown Chicago to the Illinois River: the sandstone butte and overlooks at Starved Rock, French, Wildcat and St. Louis canyons, lunch at the 1930s Starved Rock Lodge, the lock and dam across the river, and the waterfalls of the Matthiessen Dells, timed around the weekend parking-lot closures.

11–12 hour day·About 4 hours of driving in total
Best: Late March to May, or mid-October
$4 USD
A wide, empty sand beach curving along Lake Michigan under a blue sky, with white-capped waves on the right and a wooded dune in orange and red fall color rising on the leftDunes, beaches & lakeshore
Chicago → Indiana Dunes State Park → Visitor Center → Chesterton → Century of Progress Homes → West Beach

Indiana Dunes

A lakeshore day from downtown Chicago: the 3 Dune Challenge over the three tallest dunes in Indiana Dunes State Park, passes and maps at the Indiana Dunes Visitor Center, lunch in downtown Chesterton, the 1933 World's Fair houses on Lake Front Drive in Beverly Shores, and the Dune Succession Trail at West Beach, with the Chicago skyline across the water.

9–10 hour day·About 2 hours 30 minutes of driving in total
Best: September to mid-October
$4 USD
The long tile-roofed Riviera building and tour boats at their docks across a calm blue bay, with wooded shoreline and houses behindLake town, boat tour & shore walk
Chicago → Riviera Docks cruise → Downtown Lake Geneva → Geneva Lake Shore Path → Yerkes Observatory → Big Foot Beach State Park

Lake Geneva, Wisconsin

A summer day on Geneva Lake, about two hours from downtown Chicago: a morning boat tour from the Riviera Docks past the Gilded Age estates (on the U.S. Mailboat in season), lunch downtown, a walk on the public Shore Path from Library Park, a tour of Yerkes Observatory in Williams Bay and a late swim or walk at Big Foot Beach State Park.

11–12 hour day·About 4 hours of driving in all, most of it the round trip from Chicago
Best: Mid-June to mid-September
$4 USD
A footbridge with black iron railings crossing the grassy levee toward downtown Galena, where brick buildings and church steeples climb a wooded hillside under puffy white cloudsHistoric small town & long road trip
Chicago → Horseshoe Mound → U.S. Grant Home → Grant Park → Main Street → Old Blacksmith Shop → Chicago

Galena

A long day from Chicago to Galena, the 1850s lead-mining river town in the far northwest corner of Illinois: a hilltop preserve with views into three states, a tour of the house Galena gave Ulysses S. Grant in 1865, a walk over the river to the brick storefronts of Main Street, and a working 1897 blacksmith shop.

12–13 hour day·About 3 hours each way via Interstate 90 and US 20; little driving once you are in Galena
Best: May to October; best on Friday to Sunday
$4 USD
Two red vintage gas pumps in front of the white clapboard Ambler's Texaco station in Dwight, with a green roof, shuttered window and flower box under a deep blue skyRoute 66 road trip
Begin Route 66 sign → Joliet → Gemini Giant → Polk-A-Dot Drive In → Ambler's Texaco → Odell Standard Oil → Pontiac

Illinois Route 66: Chicago to Pontiac

The first hundred miles of the Mother Road in its centennial year: a photo at the Begin Route 66 sign in downtown Chicago, Joliet's Route 66 Welcome Center and the 1926 Rialto, the Gemini Giant in Wilmington, burgers at Braidwood's Polk-A-Dot, two restored 1930s gas stations in Dwight and Odell, and the Route 66 Hall of Fame in Pontiac.

10–11 hour day·About 200 miles and 4½–5 hours of driving in all, out on old Route 66 and back on I-55
Best: May to October
$4 USD

Every guide lists the date and time it was last updated and when the trip is best experienced, from a single week to all year. Each includes official links to verify roads, tides, hours, fees and closures for your travel date. Buy once and the guide is yours forever: read it online any time from your account, always in its latest version, or keep it offline in the Greg’s Guides app for iPhone and iPad, which updates it for you.

A little preparation goes a long way.

All the useful stuff.
In one little guide.

No juggling a dozen tabs or guessing how much you can squeeze into a day. Get a realistic starting plan, then make the day your own.

  • No ads. Just your next great day.You’ll never see ads popping up in your face to ruin your experience. Our website, app and guides are ad-free, so you can focus on planning and enjoying your trip.
  • Your day, laid outA timed itinerary, worthwhile stops, and honest driving estimates.
  • Your route, readyA route overview plus Google Maps, Waze, and Apple Maps links. Open a route to use your app’s latest available road closures, detours and traffic information.
  • The details that save a headacheParking, park rules, seasonal closures, packing tips, and what to skip.
  • A plan for the unexpectedWeather alternatives and flexible stops when the day runs long.
  • Dated, seasonal and yours to keepEvery guide shows when it was last updated and when the trip is best experienced. You own your guide forever: read the latest version online any time, or keep it offline in our iPhone app.
GREG’S GUIDES IN EVERY GUIDE
One guide.
A better starting point.
01
Trip guideRead online or in the app
✓
02
Route overviewSchematic route map
✓
03
Navigation linksGoogle Maps · Waze · Apple Maps
✓
04
Offline in the appiPhone & iPad, no signal needed
✓

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Guides in the app work offline. Navigation needs a connection or maps saved in your navigation app.

From “we should go somewhere” to out the door.

Your next good day in three steps.

01

Pick your escape

A relaxed beach day, a mountain outing, or a bigger coastal adventure. Choose what fits your time.

02

Get your guide

Pay once and read it online right away, or open it in the Greg’s Guides app to keep it on your phone.

03

Make a day of it

Check current conditions, open your route, and head out. Linger where you like. Skip what you don’t.

Good questions.

A few things
before you go.

What exactly am I buying?

A digital guide with a timed itinerary, stop-by-stop details, a schematic route map, navigation links and a plain-text plan. This is a self-guided plan; attraction admission, parking, food, and transport are separate. We update trips regularly, and you’ll always have access to the latest information: you own your guide forever, so you can read the latest version online any time or keep it up to date in the app.

Do I need an account?

No, but it’s worth having. Tell us your home city and we’ll unlock a free guide to a day trip, event or activity near you. Your account also keeps every guide you buy, so you can read it online any time and use it in the Greg’s Guides app.

Will it work on my phone?

Yes. Read it online in your phone’s browser: sign in to My account and open your guide. Or, as we recommend on iPhone and iPad, use the Greg’s Guides app: sign in with the same account and your guides are saved on your phone, so they work without cell service. Navigation links open in the relevant app or browser when supported.

Can I use the guide without cell service?

In the Greg’s Guides app, yes: your guides and route maps are saved on your phone. Reading online needs a connection. Guides don’t include offline road maps or turn-by-turn navigation, so save the area in your navigation app and prepare your route while connected.

Will my route include current closures and detours?

Route links open in Google Maps, Apple Maps or Waze, which calculate directions using their latest available road, traffic, closure and detour information. This information depends on your app, coverage and connection and may not include every restriction. Check official road alerts, review the route before leaving and obey posted closures. The guide’s route map is a saved overview.

Are these trips suitable for everyone?

Each preview tells you the time commitment and activities. Beach sand, stairs, steep paths, weather, and road access can affect suitability. Choose shorter options and check accessibility at the stops you want to visit.

How current is the information?

Each guide shows the date and time it was last updated and the time of year it is best experienced; some stops also note their own best season. Roads, services, prices, tides and rules can change, so every guide includes official sources to check before departure. Online, you always see the latest version, and the app updates the guides on your phone. You own your guide forever.

How do I get my guide after paying?

Stripe returns you to an order page with links to read each guide online as soon as payment is verified. Bookmark that page and reopen it any time for fresh links. Sign in or create a free account to keep your guides together and use them in the Greg’s Guides app. No subscription is required. Please keep the order link private.

Who is Greg?

I’m Greg Pasquariello, a software engineer living in the Pacific Northwest and the owner of Tecnicl LLC. I love a good day trip, and I host a lot of out-of-town visitors who want to know what they can do while they’re here. Greg’s Guides began as the plans I kept putting together for them. Now anyone can use them.

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