Weekend in Chicago: A Veteran's Guide to the Windy City

If you’ve seen the tourist traps, you know that it’s time for a change when you head into Chicago for the third, fourth, fifth, or five-hundredth time. With Willis Tower, Cloud Gate, and the Art Institute crossed off the list, it’s time to delve into the city’s hidden gems. Book a charter bus rental in Chicago to customize your next trip.

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Returning to Chicago

Whether you’re taking a break from your business trip with coworkers, exploring a new city with family, looking for field trip ideas, or even planning a day out for your retirement community, Total Charters has you covered. We’ll help plan the logistics of your trip, ensuring that you have plenty of time to enjoy each stop and get around the city with ease. With minibuses, charter buses, and options in between to suit all types of groups, we’re your #1 choice for all of your Chicago group travel.

Below, we’ve gathered a sample 2-day itinerary of Chicago favorites, plus some hotel recommendations and restaurants to include-- all approved by both locals and seasoned tourists. Check it out and see if you’d like to experience a similar trip with your own personal charter bus! Or, you can choose what stops best suit your group’s interests. When you travel with us, you’re always in control.

The front sign at The Chicago Theatre

Where to Stay:

For this trip, we recommend staying at a local Bed & Breakfast rather than a chain hotel for a more cozy, intimate atmosphere. Odds are the lodging will be operated by a local family who can make even more recommendations regarding food, drink, nightlife, and more.

Villa D’Citta

Phone: (312) 771-0696

Address: 2230 N Halstead Street, Chicago, IL 60614

House 5863 Bed & Breakfast

Phone: (773) 682-5217

Address: 5863 N Glenwood Avenue, Chicago, IL 60660

Villa Toscana Guest House

Phone: (773) 404-2416

Address: 3447 N Halstead Street, Chicago, IL 60657

Old Chicago Inn

Phone: (773) 472-2278

Address: 3222 N Sheffield Avenue, Chicago, IL 60657

How to Get Around:

Public transportation, rideshare services, taxis, and cars can leave your group separated and cause some members to end up lost or late. With a private bus, everyone can travel together without the stress of navigating city streets. Your driver will make sure that you arrive on time to every attraction. You can relax and enjoy every part of your trip when you have private transportation courtesy of Total Charters.

Where to Go:

With the tourist traps out of the way, it’s time to hit some of Chicago’s lesser-known gems. You’ll still be able to enjoy what makes Chicago unforgettable; the only thing missing will be the hectic crowds. Try these destinations on your next trip:

Day 1


Milton Lee Olive Park

Address: 511 N Columbus Drive, Chicago, IL 60611

With plenty of grassy area, jogging paths, biking paths, and a few fountains, the Milton Lee Olive Park is the perfect place to relax within the city while still feeling secluded. Offering a gorgeous, quiet view of the skyline, it’s also a great alternative to tourist traps such as Willis Tower.


Busy Beaver Button Museum

Phone: (773) 645-3359

Address: 3407 W Armitage Avenue, Chicago, IL 60647

This niche museum holds an astounding collection of, you guessed it-- buttons. The museum’s unique exhibit demonstrates the ways in which people have been using buttons to express opinions, show their support for causes, and remember special events since the pinback button was patented in 1896.


Chicago Fire Soccer Game at Toyota Park

Address: 7000 Harlem Avenue, Bridgeview, IL 60455

If you’ve gotten your fill of Chicago baseball or you just don’t find yourself interested in America’s pastime, try a soccer game at Toyota Park. Your driver will bring your group out to Bridgeview for the game, and will be ready to transport you safely back to Chicago once the game’s over.

A man and woman look out at the water with the skyline in the background at Milton Lee Olive Park, Chicago.

Day 2


Field Museum of Natural History

Phone: (312) 922-9410

Address: 1400 S Lake Shore Drive, Chicago, IL 60605

While other museums such as the MSI and Art Institute attract the majority of tourists (and rightfully so), the Field Museum of Natural History offers both permanent and traveling exhibits, including the largest and most complete Tyrannosaurus rex fossil ever found. Both adults and children will love spending a morning exploring the museum’s breathtaking exhibits.


Woolly Mammoth Antiques & Oddities

Phone: (773) 989-3294

Address: 1513 W Foster Avenue, Chicago, IL 60640

An extremely unique shopping experience that’s  sure to leave a lasting impression, Woolly Mammoth Chicago features amusing and eclectic oddities you won’t find anywhere else. From objects modeled after body parts to various books, toys, skulls, and more, this is your stop for abnormal souvenirs to bring back to your friends.


The Hideout

Phone: (773) 227-4433

Address: 1354 Wabansia Avenue, Chicago, IL 60642

Located in an old 19th-century house, The Hideout opened as a bar in 1934 after prohibition officially ended. Though it’s tucked away amongst empty lots and old factories in the North Branch Industrial Corridor, The Hideout is consistently ranked as one of the best bars and music venues in the country.

What to Eat:

While Chicago-style pizza and hot dogs are always a must, don’t forget to give some love to other local restaurants. We’ll help you schedule stops at all of your top restaurant choices when you call to book your bus, ensuring that you’ll have plenty of time to enjoy every meal and still make it to every stop on your itinerary on time. Here are just a few suggestions we’d like to make to complete your next trip:

A group of people laughing and having conversation.

Smoque BBQ

Phone: (773) 545-7427

Address: 3800 N Pulaski Road, Chicago, IL 60641

Craving some classic BBQ from back home? Smoque’s is some of the best in Chicago, rivaling even the true BBQ kings of the Carolinas.

Dusek’s Board & Beer

Phone: (312) 526-3851

Address: 1227 W 18th Street, Chicago, IL 60608

For brunch, lunch, dinner, or a late-night bite, Dusek’s is a local favorite and remains relatively unknown to the tourist crowd.

Tank Noodle

Phone: (773) 878-2253

Address: 4953-55 North Broadway, Chicago, IL 60640

Enjoy authentic Vietnamese cuisine at Tank Noodle, a family-built restaurant that offers a cozy and relaxed atmosphere.

Pro Tip: Plan Your Trip Around a Festival

To experience even more of Chicago’s best, try to plan your trip around a festival or other city event for a taste of local food and a chance to mingle with those who love the city as much as you do.  Here are a couple of examples our passengers have loved in the past:

Lakeview Taco Fest

Address: 3500 N Southport Avenue, Chicago, IL 60657

Over a dozen local eateries gather at the annual Lakeview Taco Fest to see who can craft the best tacos. Accompanied by tastings of seasonal beers, this festival is sure to pack a fun-filled weekend.

Garden Chef Series

Address: 1000 Lake Cook Road, Glencoe, IL 60022

Featuring a different restaurant and chef every weekend from May through October, the Garden Chef Series showcases some of Chicago’s best food, and offers plenty of opportunities to try new dishes.

Travel in Chicago with a Personal Bus

Total Charters makes it easy to travel to Chicago with your group. Our simple, efficient reservation process and our network of modern, reliable charter buses make us your #1 choice for all of your Midwest travel. To secure transportation for your next trip, call our reservation specialists at 312-766-2242. We’re available 24/7 and always ready to provide you with a free, no-obligation quote!