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|Updated on October, 28,2024|

If you’ve never visited Chicago before, ‘How to Spend the Best Time in Chicago’ is your guide! Chicago is a city that can’t be missed. It is so beautiful at any time of the year and offers a lot of things to do for every preference and budget.

 

The best time to visit Chicago is from May to the end of October. When the weather is nice, and there are still lots of outside activities to do.

 

Let me tell you a short story about how I got here. In my first three months in America, I lived in Pennsylvania Harrisburg, and despite those funny and fulfilling summer months, I came back home with the idea of going back the following year, but. I didn’t want to come back to the same place. So I started my research on where else can I go, and that’s how I found out about Chicago, and I loved it just from the pictures I saw. So I decided to give it a try, and here you go. I have stayed here since then and never looked back. This city is perfect for just tourists to visit as for people who want to move here.

 

Once you visit Chicago, you will immediately fall in love with the city.

 

Did you know that we have the best downtown in the USA? Yes. It is constantly updated with new cool stuff, which makes you never get bored, even if you live here.

How to Spend the Best Time in Chicago: Ultimate Travel Guide

 

What to Know About Chicago

1. Chicago is known for its winds (which can be so strong, and that is true), but its nickname “Windy City” not only related to the winds, but refers to its politicians’ reputation for long-windedness.
2.  Chicago-style (deep dish) pizza
3. Jazz music
4. 1920s gangsters
5. Famous hot dogs
6. Chicago is home to the world’s first skyscraper, the Home Insurance Building, built in 1885.
7. The historic Route 66 starts in Chicago, making it a popular spot for road trip enthusiasts.
8. There are two main airports in Chicago: O’Hare (North Chicago) and Midway (South Chicago)
9. The main shopping areas in Chicago are the Magnificent Mile (Michigan Avenue) and West Loop (State Street)

How to Navigate Around Chicago?

1. This is the most straightforward question to answer. Chicago has a unique transportation system that works mostly 24/7 (despite specific routes). We have different train lines: Blue, Red, Orange, Green, Purple, and Brown. The blue line goes straight to O’Hare airport, which makes traveling to and from the airport very convenient, it is also 24/7.

Tip: Avoid using the Blue Line or any other lines late at night unless necessary, as you may encounter many homeless people there and it’s not safe at night in general.

 

2. Do you not like trains? No worries, use the bus instead. You can buy a bus pass (for 1, 3, 7 days, or 30 days) which will be valid for buses and trains. A one-way ride will cost you $2.50 on the train and $2.25 on the bus. All other transfers (up to 2 additional rides within 2 hrs) are just $0.25. These are the summer prices for 2021. Regular prices will be slightly higher depending on the person’s age and sometimes the season. Traveling from O’Hare has a special price, which is $5. Byung passes are easy. You can do it at any CTA station and, after that, load more money online (if you download the Ventra app).

 

3. Another way to travel is by taking Lyft or Uber. They are everywhere now. These days, they might be a bit expensive, but if you need to travel a short distance, they can be cheap.

Tip: Always compare prices for two apps, as you can find better prices with one or another.

 

4. A bike ride is also a good option. Divvy stations are everywhere around the city. You can unlock your bike online (by using the Lyft app) or pay at the station. A single ride will cost you about $4 (tax included).

 

5. Regular taxis. They can be more expensive, but if you are in a rush and see a taxi on the street, wave your hand, and they will take you, if available.

 

6. Car rent. I do not recommend renting a car in Chicago since all the sights are located downtown or not too far away and can be accessible by public transport, but if you plan to go outside of the city, that might be a better option.

 

What Are Good Neighborhoods in Chicago to Stay and Visit?

As you might have heard, Chicago has a reputation for crime, but don’t let that deter you from visiting. While some areas, like the South Side, can be less safe, most neighborhoods are quite secure.

Here is the list of good neighborhoods to stay in Chicago or visit:

 

1. Gold Coast

This lovely neighborhood is very close to Downtown, the lake, and the beach. It has many boutique shops, the famous Rush Street, luxury restaurants, upscale hotels, bars, clubs, and more. By the way, many rich people live there.

Top Hotels to Stay in Gold Coast

• The Drake (from $177)
  This historic hotel is located on the Gold Coast and within a very short distance of the Observatory deck, plus it has a rooftop.
• Acme Hotel Company (from $105)
  This boutique hotel is in the perfect neighborhood close to all famous Chicago landmarks.

• Hyatt Centric Chicago Magnificent Mile (from $152)
  Great hotel which offers not just lovely and comfortable rooms, but also workspaces. Plus, it is located in the middle of all attractions.

2. Lincoln Park

This neighborhood is home to the Lincoln Park Zoo, a small botanic garden, and lovely walking paths with great views. It’s perfect for families with kids and budget travelers. Direct buses are available to take you from Lincoln Park to Downtown.

The Best Hotels to Stay in Lincoln Park and Near

• Hotel Lincoln (from $114)
  This upscale boutique hotel with an eclectic-meets-collegial vibe is just within a short distance from the Lincoln Zoo and Lincoln Park.

• Hotel Versey Days Inn by Wyndham Chicago  (from $84)
  This hotel is also located in the middle of all activities, and in case you want to use a gym (consider there is no gym at the hotel), there is an LA Fitness just next door.
• W Chicago Lakeshore (from $172)
  This hotel is the perfect location, as it is just across the lake and beach, which also offers stunning views.

 

3. Logan Square

Known for its hipster vibe, this area has a unique character with mural art, vintage shops, parks, and restaurants. While it might not be the best place to stay due to limited activities, it’s worth visiting.

 

4. River North

Another very nice neighborhood to visit. Here is where you can see a lot of clubs, bars, and restaurants. You can party the whole night and have an early breakfast in one of the places open 24/7. Also, this neighborhood has several art galleries in the entire United States.

 

Another good thing about this area is that it is very close to the Magnificient Mile,  known for all the leading shops in Chicago. So in the summer, you can walk from River North to Magnificent Mile or other great neighborhoods, such as Gold Coast or Streeterville, and explore the beautiful scenery.

The Best Hotels to Stay in River North and Near

• Royal Sonesta Chicago Downtown (from $161)
  This is the trendiest and most distinctive hotel, located within a short distance from Millennium Park, Michigan Avenue, Chicago Riverwalk, Navy Pier, and more.
• Embassy Suites Chicago Downtown (from $156)
  This family-friendly hotel is a great place to explore the city on foot since it is also close to all major attractions and relax after a long day of walking.
• The Godfrey Hotel Chicago (from $135)
  This boutique hotel in the trendy River North neighborhood offers excellent accommodation and a year-round rooftop with DJ.

 

5. Streeterville

Close to River North, this area features a Navy Pier, known for its stunning water views, excellent dining options, and the iconic Ferris wheel. From Navy Pier, you can easily walk to Gold Coast, Downtown, Loop, or River North, as they are all nearby.

The Best Hotels to Stay in Streeterville and Near

• Hyatt Centric Chicago Magnificent Mile (From $152)
  This is the perfect spot in the city to explore all attractions on foot.
• The Sono Chicago (From $199)
  This boutique hotel offers bed-and-breakfast and is located in the heart of the historic Old Town.
• Hampton Inn & Suites Chicago Downtown. (Price starts from $130, which includes a 10% discount if you book with Hotels.com). This hotel is located steps away from Michigan Avenue (the avenue full of clothing stores) and more.

 

6. Lakeview (Boystown)

This area is considered home to the pre-eminent gay, lesbian, bisexual, and transgender communities of Chicago. The neighborhood is charming, with many bars, restaurants, and other places. Also, it is close to the lake, parks, and Wrigley building, where all the Cubs games occur.

 

________________

• Chicago luxury neighborhoods: River North and Gold Coast
• The most significant area for budget travelers: is Lincoln Park
• The best place to experience nightlife: is River North. Since all sightseeing is located downtown or around, it is better to stay in Gold Coast, River North, Streeterville, or Lincoln Park, so you can walk to the places you need or take a short ride.

Best Hotels to Stay Near the Airports

O’Hare

• Loews Chicago O’Hare Hotel (from $127)
  This luxury 4.5-star hotel is located near the O’Hare airport and Rosemont Theater. This can be the best option to spend a night if you arrive late.
• The Rose Chicago Tapestry Collection by Hilton (from $101)
  This boutique hotel is located in the heart of the Rosemont District, close to O’Hare airport. You can make sure that your stay here will be pleasant and unforgettable.
• Hampton Inn & Suites Rosemont Chicago O’Hare (from $117)
  Great place to spend a night. Close to the airport and Rosemont attractions.

Midway

• Courtyard by Marriott Chicago Midway Airport (from $139)
  The convenient location to the Midway airport (just a 5-minute drive) makes this hotel the best option to spend a night. It offers an indoor pool, restaurant, airport transfer, and more.

• Hyatt Place Chicago/Midway Airport (from $138)
  Great place to stay near the Midway airport (2 min drive). They offer many good amenities, such as an indoor pool, restaurant, free parking, and more. Look no further and book your room there if you fly to Midway.
• DoubleTree by Hilton Chicago Midway Airport (from $141)
  This hotel is located just a mile from Chicago Midway International Airport, which is about 5 5-minute drive. They also offer their guests an indoor pool, restaurants, and other great amenities.

  All these hotels are under $200 before taxes, the lowest nightly price for a hotel in Chicago. However, please remember that prices will always be different, and these are just approximate estimates per night, which depend on the number of people and the day.

   

  For a more budget option, check out the list of best Hostels to stay in Chicago below.

The Best Hostels to Stay in Chicago

1. Wrigley Hostel ($31 and up)
This hostel is located in the heart of Wrigleyville and near Lincoln Park and Lakeview. Plus, it is just a 10-minute walk from the beach, and all public transportation is near.

2. Chicago Getaway Hostel($25 and up)
This hostel is located right in the heart of Lincoln Park. Great location, which lets you walk everywhere.

3. HI Chicago, The J.Ira & Nick Harris Family Hostel (from $73 and up)
This hostel is located in downtown Chicago, the Loop area. The area is full of businesses and, nowadays, also residential buildings. A loop is not the best area to walk alone, but it is not that bad. You can find lots of places to visit and go shopping. It is just a 9-minute stroll from Grant Park and a 15-minute walk to the observation deck of Willis Tower.

4. Freehand Chicago (from $62)
This hostel is located in the center of River Noth and close to Downtown, Gold Coast, Streeterville, and Loop, which makes it the best location.

5. FOUND Chicago River North (from $95)
This hotel has three stars, and since the price is meager compared to others, it is often considered a hostel. However, nothing can beat the location, especially if you travel on a budget. This place is not an exception as it is cheap and located in the heart of River Noth. From where you can walk everywhere and not spend time and money on transportation. Plus, it is a very safe neighborhood.

 

To get more info about Chicago hostels, check out this post Best Hostels in the USA.

 

Related topic:
|How to find a cheap hotel

Where Not to Go and Not to Stay in Chicago

• West/East Garfield Park
• Washington park
• North Lawndale
• Riverdale
• Englewood
• Chatham
• South Shore
• Burnside
• South Deering
• Pullman
• South Chicago
• Fuller park
• Auburn Gresham
• Gage park
• Chicago lawn

|You MUST avoid these areas|

What to Do in Chicago in the Summer

Omg, summer in Chicago is the best time of the year. It is sunny and warm and lots of activities to do outside.

Here are the best summer activities I recommend you do once you visit:

1. Chicago River Architecture Cruise: Skip-the-Ticket-line

2. Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

3. Chicago: Hop-on, Hop-off Open-Top Bus Tour

4. Explore Millenium Park and take pictures of the famous bean

5. Visit summer festivals

6. See the Buckingham Fountain

7. Walk or bike on the Lakefront Trail

8. Visit Riverwalk

9. Walk The 606

10. Visit Chinatown

Things to Do in Chicago When it’s Cold

Came to Chicago when the temperature was already down and wondered what to do? Do not worry. This city got you covered on cold days as well. There are plenty of things to do indoors, which are also fun. Here is the top list:

1. Visit the Chicago Laugh factory

“I’ve been there once, and I was surprisingly excited. We had so many laughs and a great time. The tickets are free (if you ‘buy’ them on Eventbrite, though there is a mandatory $20 fee that covers two drinks).”

Get your tickets to the laugh factory here.

2. Discover a New Skill 
Take a painting, pottery, soap making, or other class. You will find a good selection of them on Groupon.

3. Listen to Live Music
Enjoy live jazz music and Green Mill. An entrance ticket will cost you less than $20, and they only accept cash.

4. Play Games
Want to go somewhere for a drink? Combine it with fun games instead of just sitting in the bar and drinking.

Check out Headquarters Beercade, where you will find plenty of fun games.

 

5. Visit a Car Museum
Check out the vintage cars museum “Klairmont Kollections.” Believe me, if you have never been to such a museum, it is an excellent experience. I’ve been there once, and I should admit it is worth every penny (price$15 – $49.95).

6. Visit the St. Patrick Parade

I am going to include one more activity on this list. It is not indoors, but worth seeing if you are in the city on St. Patrick’s Day (March). Early in the morning, the river gets dyed a fantastic bright green. There is also a parade, which happens the Saturday before St. Patrick’s Day. It starts at Balbo and Columbus and continues north to Monroe.

 

Prepare to see lots of drunk teenagers wearing all-green clothes. Although it can get very crowded, I highly suggest experiencing it at least once. After the parade or watching the green river, you can end your day in one of the bars or restaurants, where it will also be very noisy but fun.

Related topic:

|20 best getaways near Chicago

Free Things to Do in Chicago

1. Visit the City Gallery near the Water Tower
It is well known as one of the few buildings that survived the destructive path of the Great Chicago Fire in 1871. The gallery is located inside the Water Tower and represents the venue with the work of local photographers and artists.

 

2. Explore Garfield Park Conservatory
Garfield Park Conservatory is one of the largest botanical conservatories in the nation. It is an 184-acre park with tennis courts, a fishing lagoon, a pool, athletic fields, and more.

 

3. Wander at Lincoln Park Conservatory
Located near Lake Michigan, within walking distance of the lake and beach. Step inside and explore four sections inside the conservatory: Palm House, Fern Room, Orchid House, and Show House, which are full of plants, flowers, and trees.

 

4. Visit the Lincoln Park Zoo
Lincoln Park Zoo is the fourth oldest zoo in North America. It is located right in the heart of Lincoln Park.

 

5. Check free museums: Chinese American Museum of Chicago, Smart Museum of Art, National Museum Of Mexican Art,
National Veterans Art Museum, The Oriental Institute Museum, The Renaissance Society, the National Museum Of Puerto Rican Arts & Culture, the Museum of Contemporary Photography, the DePaul University Art Museum, and the Chicago Children’s Museum.

 

6. Free movies in Millenium Park in the summer
What can be better than relaxing on a lovely summer evening and watching a movie in the open air?!

Tip: Come early to get a better seat. Get more info here.

7. Visit Chicago Cultural Center
Chicago Cultural Center is one of the most visited attractions in Chicago. The beautiful landmark building has two magnificent stained-glass domes, music and theater events, films, art exhibitions, lectures, and family events.

8. Get lost in the Chicago Botanic Garden
Explore millions of beautiful and rare plants, trees, and flowers on the 385 acres of garden.

9. Visit Revolution Brewery
You can take a free brewery tour at Revolution from Wednesday through Friday. First-come, first-served basis.

10. Discover Maxwell Street Market
You can visit Maxwell Street Market every 1st and 3rd Sunday from 9 am–3 pm. You will find a mix of handmade crafts, housewares, clothing, and more.

 

11. Watch Navy Pier Fireworks
Navy Pier has free fireworks every Wednesday and Saturday night in the summer and Saturday night in September. I highly suggest checking it out.

 

12. Taste of Chicago To-Go
Visit the free-admission food festival in Chicago. Where you will have a chance to taste different foods for every taste.

 

13. Chicago Air and Water Show
Every August, you can watch the fantastic Air and Water Show. If you are in the city, you must be near Oak or North Beach to experience this great event.

14. Magnificent Mile Lights Festival
Take your opportunity to watch the amazing, world-known lighting festival in the Magnificent Mile. Enjoy the city lighting along with music and the holiday atmosphere.

Things to Do Near Chicago

If you have some extra time, I highly suggest visiting these places:

 

1. Visit the billionaire neighborhood, Wilmette.

Walk around the quiet streets, check out the beach, and admire the beautiful Bahá’í Temple.

2. Explore  Evanston. Explore the charming city of Evanston, a suburb of Chicago, known for its beautiful beaches, vibrant history, and diverse food scene. Enjoy a stroll through its scenic streets, relax on its lovely beaches, or dine at its numerous restaurants.

Money-Saving Tips in Chicago

If you’re used to big city prices, Chicago won’t be a shock, but as with any city, accommodation, attractions, and food can add up. Here are some smart tips to save money:

• Try Couchsurfing instead of staying at hostels or hotels. It’s free.
• Take advantage of free walking tours.
• Buy a CTA pass instead of paying for single rides.
• Take advantage of free museum days
• Look for happy hour deals
• Rent a bike to explore the city
• If you arrive in Chicago late in the evening or at night, book a hotel near the airport. The CTA isn’t very safe at that time, and Uber can be expensive ($70-100).

 

Final Thoughts

Chicago should be on everyone’s list of top cities to visit in the USA. If you haven’t seen this beautiful city yet, you should plan a trip now. Navigating in Chicago is super easy and affordable with plenty of public transportation, bikes, scooters, taxis, Uber, and Lyft available.

 

The best times to visit Chicago are in the summer and spring. Even in the colder months of late fall and winter, there are still plenty of things to do, such as visiting museums, galleries, botanic gardens, and more. There are always enough activities to suit every taste, budget, and season.

 

I hope you found the information in my Ultimate Chicago Travel Guide useful. Now you know how to make the most of your time in Chicago.

 

If you have questions about Chicago, I will be very glad to answer. Thank you for stopping by. Happy travel!

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