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Within minutes you can go from shopping designer brands on Michigan Avenue to enjoying some fun in the sun and sand. By now you can see that a trip to the Second City is really second to none. Without a doubt, any local will agree that the best time to visit is in the summer June-September. Although Chicagoans will tout surviving blizzards and sub-zero cold snaps like a badge of honor, everyone lives for the season of rooftop happy hours, beach volleyball, and countless street and music festivals.

Gay Chicago: A Gay Travel Guide to the Windy City

No matter the time of year, Chicagoans will welcome you with midwest charm and hospitality. Servicing the Chicagoland area including 35 suburbs and the city of Chicago, you can quickly get around town using the expansive train and bus system. Between the busses and trains, you can find a way to get from point A to point B with relative ease.

For additional CTA fare and ticket prices click here. For information on the Ventra card and app to manage it, click here. In addition to safe and reliable public transit, ridesharing apps like Lyft and Uber are very popular and the service is widely available in the city and surrounding suburbs. Although dedicated lanes cordoned off from the downtown traffic are increasing, most bike lanes are shared with city busses. Even the most experienced city cyclists run into trouble on the busy streets.

Bike rentals are a plenty through Divvy Bike with stations and 5, bikes across Chicagoland where you can checkout bicycles. The airline and various other factors will determine which airport you fly into. Both, however, are easily accessible to downtown and the rest of the city. Be aware of those late night arrivals and early morning departures as the Orange Line runs all day, everyday except from about 1am to 4am Monday — Saturday and after 11pm on Sundays.

During these overnight hours, alternate transportation is provided by the N62 Archer bus. Car rentals are available at both airports, but a car is not required to enjoy the Chicagoland area and many residents rely exclusively on public transit.

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With that in mind, it may be wise to skip the rental car and take the CTA or other options like Uber, Lyft, and taxis. Guesthouse hotel Andersonville — named one of the best boutique hotels in Chicago by Time Out, this family-run establishment makes you feel like a local before you even arrive with their welcome email giving you the on what to do and where to go. If in-house afternoon tea at a posh getaway from the tourist sites downtown sounds like your cup of tea, the Guesthouse hotel in Andersonville will not disappoint.

Rest assured that this classic English manor style is paired flawlessly with modern amenities such as complimentary access to a neighboring fitness facility, continental breakfast, and a fully stocked mini bar. Villa Toscana Boystown — if you want to be in the center of the action, then this charming guesthouse in the heart of Boystown is second to none! Built in , this Victorian structure boasts old world European charm as each room is tastefully adorned in a different style from French to Moroccan. At the same time, the inn has all the expected modern amenities such as complimentary wireless Internet and continental self-service breakfast.

The Villa can accommodate guests from a couple to a large group.

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However, you must reserve well in advance as it sells out quickly, especially during peak times like the Pride celebration and Market Days. Best Western Plus Hawthorne Terrace Hotel Boystown — leave any preconceived notions of a standard hotel chain at home and prepare to be impressed. City suites Hotel Boystown — just steps from the Belmont red line connecting you to downtown and a few blocks away from the nightlife of north Halstead, this modern hotel features art deco inspired decor and colorful accents.

Take a closer look at the fine details such as custom-made wood headboards, wardrobes, and desks as well as the fully stocked mini bar and separate sitting rooms in the suites. From the fun and friendly rooms with ample amenities to the superb location, City Suites Hotel is an ideal pick for a weekend in the windy city. Imagine matching hotel-style service with great deals in an ideal location. Check out the amenities such as free WiFi, communal kitchen, daily breakfast and free coffee, and weekly social events and guest lockers. You have a choice of private rooms with shared baths, private rooms with ensuite baths, and bunkrooms for four to 12 people.

For the budget traveler, this clean and modern hostel will fit the bill without breaking the bank. Wrigley Hostel Wrigley — let your inner baseball fan out and stay in the heart of the action at this Wrigleyville hostel. Choose accommodations from a private room to an eight-bed dorm-style room with bright colors and hardwood floors. Enjoy all the amenities such as secure guest lockers, free Wifi, and complimentary breakfast. Whip up your favorite dish in the fully equipped kitchen and lounge on the outdoor patio and grill. Special offers: This is especially true with its diverse neighborhoods that feature food and culture from around the world.

Art Institute of Chicago — named the best museum in the world by Trip Advisor in , the collections at the art institute contain about , masterpieces with temporary exhibitions opening several times throughout the year. All the way up on the rd floor, the Skydeck features retractable glass balconies that allow you to stand on a four-foot glass ledge looking down to the street 1, feet m below.

In the summer, enjoy live music and performances on the lawn of the Jay Pritzker Pavilion and in the winter strap on a pair of skates at the McCormick Tribune Ice Rink, a holiday tradition for many. Here you can enjoy small bites and sips at one of the many cafes and people watch as families, runners, and even yachts pass by. A peek inside some of these historic theaters is worth the ticket alone. Comedy and improv shows are a plenty and can cost just a few dollars per ticket.

The raw talent is truly impressive. Museum Campus — so just how do people get those fab panoramic skyline views of the city without walking on water? Head over to the Adler Planetarium for some of the most Instagram-worthy cityscape snaps. Every Wednesday and Saturday nights during the summer enjoy a spectacular fireworks display. Hop on the newly constructed Centennial Wheel taking you up feet with degree views of the city. Chicago is a perfect place to explore by foot, boat, bicycle, and even Segway! Walk aboard an architecture boat cruise, follow a docent down the the grid-like streets, or cycle on the lake shore.

Start your journey at the Chicago Architecture Foundation located at E. Wacker Drive. Architecture Boat Tour — one of the best ways to experience the rich architectural landscape of the city is by boat, cruising on the Chicago River. This is a must-do in Chicago as tourists and locals alike can be found aboard these vessels to learn about the city and admire the stunning views. There are several tour companies and each offer different types of cruises like to see the sunset, fireworks, or focus on a specific geography or topic.

Most tours are led by very knowledgeable guides who will share history, fun trivia, and point out the best photo ops. Food Tours — one way to eat your way through the Windy City is by joining a food tour. Although there are many that take place downtown targeted at tourists, venture to one of the neighborhoods for a more authentic flavor. Check out tours in places like Pilsen, Chinatown , and Little Italy for local eats and restaurants that are off the beaten path.


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These are an ideal way to discover a new part of the city while filling your belly with tasty eats. Walking, Biking, Bus Tours — there are so many ways to roam around while discovering hidden gems. Chicago is a very pedestrian-friendly city, so walking tours are very common and sometimes the best way to sightsee at your own pace. If cruising on two wheels is more your style, bike tours are the way to go. Like many other cities, the big red double-decker buses are always an option. West Randolph — often referred to as restaurant row, this stretch of Randolph just west of the expressway is a foodie mecca boasting some of the hottest new restaurants and bars.

Beware that some of these spots can book up months in advance, yet sometimes you can snag an open table during non-peak hours. Food Trucks — the food truck craze has finally made its way to Chicago. If you ever miss one, remember that most have brick-and-mortar locations you can visit, too.

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Even carnivores will be floored by the meat-free Radical Reuben and the award-winning vegan milkshake to wash it down. Boystown — the gayborhood is better known for dance floors and disco balls than a killer food scene. During one of the sets, the stylist came over to me and asked if I could wear something she brought. I did a set with the photographer and the editor really liked the photos and published them in the first issue.