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Monday, December 25, 2023

Chicago, Illinois travel guide: What to see & things to do in Chicago?

  Rajesh Kumar Rana       Monday, December 25, 2023
Cloud Gate (The Bean), Millennium Park, Chicago, Illinois
Cloud Gate, chicago, Illinois

Chicago, Illinois Travel Guide

Let's start with tourism traditions. The first is to take a photo near the Cloud Gate (“Cloud Gate”). The second is to take a walk along Lake Michigan with a cup of delicious coffee. If you failed to fulfill these plans, then you were not in Chicago. Let's take a look at the city without stereotypes and forget about famous points for a bit. Today I will tell you what to do as an immigrant in Chicago, what entertainment is there for a tourist, first time visit to chicago where to stay and where to eat deliciously.

Chicago Map USA

Ticket to Chicago: the beginning of the journey

Chicago has 2 major airports: O'Hare International Airport (10000 W O'Hare Ave) and Chicago Midway International Airport (5700 S Cicero Ave). All flights go to O'Hare Airport. The second is for domestic flights. Airplane is one of the fastest options for moving around America and other countries.

Airline services

  • Skyscanner helps you find airlines, hotels or transport and compare prices.
  • AnyWayAnyDay - allows you to buy flights, book hotels and pay for everything in the application.

Mobile roaming

There are 3 most popular carriers in the US: AT&T, Verizon and T-Mobile. They are expensive, but the best in terms of connection quality and the Internet. You can consider tariffs from Simple mobile, H2O and Ultra Mobile. They often run promotions and provide better packages. For example, for a 6 GB plan with unlimited calls and SMS, pay $30 per month with H2O wireless.

If you have arrived for a short time, then choose profitable roaming. It is easier for regular travelers around the world to choose an operator with tariffs for different countries. So, Vodafone offers subscribers a 6 GB package for 10 euros for 28 days and 300 minutes, which is available in the EU countries, Monaco, Turkey, and the USA. The THREE SIM card has a 12 GB plan for 25 euros for 30 days. Its terms are valid in more than 70 countries of the world.

Accommodation in Chicago : areas and prices

The city can be divided into several groups of districts: central (Downtown), southern, western and northern. The best place to rent is along the lake from Near North Side to Chinatown. In the center are the main attractions of Chicago - Magnificent Mile, Willis Tower, Navy Pier and others.

Chicago's Chinatown
Rooftops in Chicago's Chinatown image

The northern regions are among the prestigious places where there are many boutiques, offices and entertainment for people with a high income. Among the western ones, West Town is considered the most prosperous, the rest are less safe to live in. On the south side is the famous Chinatown, the clean and green Hyde Park, and the luxurious Kenwood.

Note! There are many problem areas in Chicago, where mostly Mexicans and African Americans live. I would not recommend renting an apartment in Greater Grand Crossing, Garfield Park, Austin, Chatham, Avalon Park, Calumet Heights, Burnside.

Sites to find housing in Chicago

  • Booking: The choice of housing, ratings, reviews, seasonal discounts, offers without prepayment.
  • Tripadvisor: Hotel selections by rating, restaurants, entertainment, airline tickets, car rental. 
  • Craigslist: Renting apartments for a long or short term, ads from locals.
  • Airbnb: Rental housing directly from the owner, apartment options for a few days or weeks.
  • Couch Surfing: Rooms, beds, air mattresses and other free offers from locals for travelers.
  • HelpX: Meals and accommodation in the city in exchange for help with household or other chores.

Tourist center options

I have been renting an apartment for a long time, so I was not particularly interested in hotels. Now I decided to look for a couple of options for you on already known sites. I chose based on price and user reviews. I set the dates November 21-22 to see offers for the autumn weekend. Among all the hostels and hotels, some of the best are:

  • HI Chicago Hostel: Loop area, Over 4 thousand reviews and a rating of 8.6 on Booking. Prices: $42 for a bed in an 8-bed room, $46 for a 4-bed room, and a double room will cost from $109 to $179.
  • Freehand Chicago: River North area. More than 3.5 thousand reviews and a score of 8.2 on Booking. Prices: $42 for a bed in a 4-bed room, from $119 to $149 for an apartment for two.
  • Warwick Allerton Chicago: Near North Side area. More than 3 thousand reviews and a rating of 8.1 on Booking. Prices range from $90 to $125 per night in a double room.


Notice when booking! The price of the room on Booking does not include: 11.9% VAT, 4.5% city tax, 1% local administrative tax.

Getting Around Chicago: Bus Ticket or Car Rental

Chicago's transportation system is called the Chicago Transit Authority (CTA). This includes buses and subways. On the official CTA website here you will find ticket prices and transport schedules. For example, a bus ride costs $2.25. It is better to buy CTA Pass for 1 ($10), 3 ($20) or 7 ($28) days.

Life hack! There are discounts for regular tickets for students. During the summer period, CTA Pass prices are reduced for everyone.


See the bus schedule for each route and in advance so as not to stand for 20-30 minutes at stops. Public transport is not in “very good condition”, so don’t expect much comfort from the trip. An owl sign at bus stops means that the bus runs all night once every 30 minutes. If you get from the suburbs to downtown Chicago, you can get into a beautiful double-decker transport, paying about $16 for round-trip tickets.

Car rental

Renting a car for a day will cost about $40-60, but there will still be taxes (for example, for insurance or a navigator). Chicago has an incredible amount of cars, just like major US cities. The biggest problem is to park the car in the center. Leaving a car for an hour can cost from $16. There are free places, but they quickly lose the status of "free". Another option is a taxi. For example, in the Uber app, you can find a private driver with a car and pay for services with a bank card.

How to rent a car while traveling in the chicago, Illinois?

Recommendation!  I Use the RentalsCars Guaranteed a good car at the best price from both leading car rental companies and local rental companies. We are happy with them, and we wish you the same.


There are 8 subway lines in Chicago and all of them are laid through the center, except for the purple one. The fare will cost $2.5. The metro opens at 4-5 am and runs until 1:00. The train arrives every 7-10 minutes.


Renting a bike is much cheaper than a car. For example, you can do this on the Internet on the site. Chicago has its own McDonald's Cycle Center (239 E Randolph), which has a shower, repair services and secure parking for 300 spaces. Monthly subscription (PRO level) - $50, yearly - $237 or $15 per day.

Landmarks of Chicago : a collection to view

The most common question from everyone who travels to an unfamiliar city is: “What to visit there?”. As almost a local, I will talk about my favorite places in Chicago. Let's take a walk together in the famous parks, look for emotions in the museum and walk near the unusual buildings of the city.


Art museums are the most popular in Chicago. Doors to the world of beautiful works are located in:

  • Museum of Contemporary Art (Museum of Contemporary Art). Adult admission costs $15. According to the gallery's rules, art is available to everyone, so it is allowed to pay less.

Among the historical museums, I remember most of all:

Immigrants from Sweden, Ukraine and Poland can look at:

  • Swedish American Museum (Swedish American Museum). Swedish lessons, learning to bake and knit, discuss films and paintings. 
  • Ukrainian National Museum (Ukrainian National Museum). A collection of folk art from more than 10 thousand items, paintings, sculptures, outfits.
  • Polish Museum of America (Polish Museum of America). A library of 100 thousand books, archives of photographs and historical documents, exhibitions of paintings.



Another part of the cultural program "What to do as an immigrant in Chicago" is to walk, looking at impressive buildings. Here is a small checklist for architecture lovers:

  • Visit the 36-story Neo-Gothic skyscraper Tribune Tower
  • Take a selfie with The Wrigley Building in the background.
  • Visit the largest library in the world, listed in the Guinness Book of Records - Chicago Public Library (Harold Washington Library Center).
  • Check out the Chicago Temple Building, a skyscraper church found only in Chicago.
  • Experience the multifunctional complex of 2 Marina City towers.
  • Gaze at the grandeur of the Cook County Jail from afar, but don't visit it. By the way, in 2017, two prisoners escaped from there, making a rope out of sheets.


  • Millennium Park: Here you can see a beautiful sunset and there is a Cloud Gate sculpture. It is called "Bean" or "Bob" because of the similar architectural form. The park hosts festivals and open-air performances by musicians.
  • Maggie Daley Park: Place for children and adults: climbing wall, playgrounds, tennis courts. In winter, the skating rink is flooded. Crossing the BP Pedestrian Bridge will take you to Millennium Park.
  • Garfield Park: There is a greenhouse with charitable entrance fees, where lectures and exhibitions are often held. The building in the park houses a dance studio, a gymnasium and a fitness club.
  • Lincoln Park: Place for cycling and running. There is a free zoo on site.
  • Humboldt Park: The Puerto American Center in Chicago is located here. Come to taste national dishes and look at folk art.

Maggie Daley Park
Maggie Daley Park

Food in Chicago: Restaurants, coffee houses, supermarkets

One of the most popular places in Chicago is Lake Michigan. Next to it, I found a couple of places where you can take coffee with you for a walk or enjoy the food and the view at the same time:

  • The Coffee Studio (5628 N. Clark St.) - tea cocktails, finely patterned coffee, donuts, homemade ice cream.
  • Uncommon Ground (3800 N. Clark St.) - breakfasts, lunches, cocktails, wine, beer, coffee.

In the heart of the Chicago Gold Coast restaurant - 3rd Coast . It serves salads, all-day breakfast, seafood, steaks and vegan options.

Websites for finding the best places

Most of the establishments I look for on Yelp, where there are ratings and reviews of visitors to restaurants, cafes, etc. Another site is Food Network On the Road. There are places recommended by the American TV channel that have been mentioned in programs such as Drive-Ins and Dives, The Best Thing I Ever Ate, Barefoot Contessa and the like.

local pizzerias

Chicago-style pizza is a special recipe for a deep-sided pie with various toppings. The main difference from the usual one is that the cheese is placed under all the ingredients. It's called "deep-dish pizza" on the menu. My three favorites:

Pizza prices range from $9 to $35 depending on ingredients and size. 

Chicago-style pizza
Chicago-style pizza
image source: Flickr/ Phil Denton

Coffee houses

  • Hero Coffee Bar (22 E Jackson Blvd) is a lamp patio spot in downtown Chicago. Espresso for $3.
  • CC Ferns (2806 W Augusta Blvd) is a coffee shop with yellow sofas and a cozy atmosphere. Espresso for $1.
  • Cupitol Coffee & Eatery (812 Grove St) is a lounge area with colorful seating for work and leisure. There are breakfasts and lunches. Espresso for $2.75.

Chicago Restaurants

Popular Mid-Range Chicago Restaurants

Chicago-style pizza and Chicago-style sausage buns are known to everyone, but Chicago restaurants can offer you even more sophisticated menus!

Get a real taste of Chicago - literally - go to some elegant American restaurant - there are plenty of them in the city. Breakfast, lunch or dinner in these establishments will cost about $20-30.

1. Hub 51

A trendy nightclub and restaurant a few blocks from the Chicago Riverfront, in the River North area, full of shopping malls and places of interest to visit. The modern design of the hall and subdued lighting create a calm atmosphere.

Menu: The restaurant serves dishes in the traditions of the American South and the North - steaks, tacos and nachos, cold appetizers, original salads and huge burgers. Sushi and roll lovers, don't miss the 50% discount from 3pm to 6pm and after 11pm. Hub51 has a separate menu for people with gluten intolerance.

  • Location: 51 West Hubbard Street Chicago, IL 60610 
  • Subway Station:  Grand (Red Line); Merchandise Mart (Purple Express, Brown metro lines).
  • Opening hours: Monday - Wednesday: 11 am - 12 am, Thursday - Friday: 11 am - 2 am, Saturday: 10 am - 3 am, Sunday: 10 am - 10 pm

2. Wishbone Restaurant

A great place for lovers of spicy and spicy South American cuisine. This is one of the favorite restaurants of the townspeople - no one will be left indifferent by large appetizing portions of delicious dishes prepared under the personal guidance of the owner.

Menu: Fluffy spring omelettes and fruit pancakes with juicy gravy are popular breakfast or brunch options. Southern-style seafood patties and chicken stew served with a traditional garnish of rice, black beans and peas and a fragrant cornmeal bun. The Wishbone menu has several delicacy items for vegetarians as well.

  • Location: 3300 North Lincoln Avenue Chicago, IL 60657
  • Metro Station: Paulina (Brown Metro Line)
  • Opening hours: Monday: 7 am - 3 pm, Tuesday - Thursday: 7 am - 3 pm & 5 pm – 9 pm, Friday: 7 am – 3 pm & 5 pm – 10 pm, Saturday: 8 am – 3 pm & 5 pm – 10 pm, Sunday: 8 am – 3 pm & 5pm–9pm

3. Smoque BBQ Chicago

The homely atmosphere of this restaurant attracts tourists and residents of the city. They cook excellent Texas-style barbecue - there are always a lot of visitors, so be prepared to wait your turn!

Menu: Connoisseurs say that the meat in Smoque BBQ is cooked to perfection: ribs, beef loin, fried chicken, sausages - all dishes are served with thick homemade gravy. Meat delicacies go well with traditional side dishes - stewed beans, coleslaw and mashed potatoes.

  • Location: 3800 N Pulaski Rd Chicago, IL 60641
  • Subway Station: Irving Park (Blue Underground Line)
  • Working hours: Monday: day off; Tuesday - Thursday: 11 am - 9 pm, Friday - Saturday: 11 am - 10 pm; Sunday: 11 am – 9 pm

4 State Street Bread & Co

A popular place for breakfast and lunch among business people working in the area. The restaurant is located in a spacious building at the Courtyard Marriott HotelRiver North. Wireless Internet will allow you to have a bite to eat without looking up from work.

Menu: Variety of gourmet dishes for breakfast and lunch. Delicious cold and hot sandwiches - perhaps the best choice in Chicago! The most popular are roast beef with spicy sauce on a fragrant onion bun and panini with chicken, cheddar cheese and bacon. A new chef's "soup of the day" is offered daily. As a light snack - healthy and tasty salads according to original recipes.

  • Location: 30 E Hubbard St Chicago, IL 60611
  • Metro station: Grand (Red line); State/Lake (for Orange, Brown, Purple Express, Green, Pink trains); Clark/Lake (Pink, Brown, Green, Blue, Purple Express, Orange subway lines)
  • Opening hours: Monday - Friday 06:30 am - 2 pm, Saturday - Sunday 7 am - 2 pm

5. HB Chicago

“Home Bistro”, as this place is called, will delight you with exceptionally cooked dishes of modern American cuisine. The restaurant is located in the Lakeview area near the Steppenwolf Theatre. HB Chicago has a lot of regulars - you can bring your own liquor here!

Menu: On Wednesdays, the restaurant serves a three-course menu at a fixed price (up to $ 30 per person) - a great opportunity for gourmets to enjoy high-level cuisine at a moderate price! Hot and cold appetizers and main dishes are prepared according to the recipes of chef Lachman, the owner of the establishment.

  • Location: 3404 N Halsted St Chicago, IL 60657
  • Metro Station: Addison (Red Line); Belmont (for Purple Express, Brown, Red trains)
  • Opening hours: Tuesday-Thursday 5:30 pm - 10 pm, Friday-Saturday 5 pm - 10:30 pm, Sunday 5 pm - 9 pm

Get a real taste of Chicago - literally - go to some elegant American restaurant - there are plenty of them in the city. Breakfast, lunch or dinner in these establishments will cost about $20-30.


If you rented an apartment, then it will be more budgetary to cook your own food. Products in Chicago are different from vegetables and fruits in India. In America, they are beautiful in the window, but absolutely tasteless in the mouth. 

The largest supermarkets:


Evening entertainment in Chicago: what to do on a Saturday


Ask the bartender for the latest Chicago news. That's why I go to cool rooftop cocktail venues. Among them:

  • The J. Parker (1816 N Clark St.). Breathtaking views of Lincoln Park from the 13th floor of the hotel. It is open all year round and every day from 17:00 to 1:00, and on weekends from 16:00.
  • ROOF on theWit (201 N State St). Lounge bar on the 27th floor of the Wheat Hotel. Wine list, Mediterranean snacks and signature cocktails. It's warm even in Chicago winters, thanks to fireplaces and glass railings. Open on weekdays and Saturdays until 2:00.
  • Vertigo Sky Lounge (660 N State St). Gorgeous views of the city at night on the roof of the Dana Hotel & Spa. In winter, the bar turns into an ice sculpture exhibition where you can enjoy a cocktail.



  • Chicago Magic Lounge (5050 N Clark St.). A place where talented wizards perform and miracles happen. Works from 5 pm. Tickets for the show are about $20.
  • LiqrBox (873 N Orleans St.). There are 4 types of cocktails on the menu, which are served in closed plastic moulds. The price of one is $12. Open from 23:00.
  • SmartBar chicago (3730 N Clark St.). Club with DJs and dance music two blocks from Wrigley Field. Works from 22:00. Tickets for the show $15-20.


An important moment of club life! You must be at least 21 years of age. Don't forget to bring your passport or driver's license to prove your age.

Other recreation

Walk along the Naval Pier (Navy Pier). There is an abundance of shops, eateries and cinemas. Ride on a boat. See the city from a height of 45 meters with a Ferris wheel ticket ($16). It is open until 20:00 from Monday to Thursday. On Friday and Saturday until 22, and on Sunday until 19:00.

Experience one of the city's festivals in Chicago. In the evening there is a special atmosphere. Music festivals in 2022:

  • Tomorrow never knows. January 20-23.
  • Chicago Blues Festival. June 3-5.
  • Lollapalooza Chicago. July 29-August 1.

You can find out more information about them and buy tickets here . Just don't rush, because the COVID-19 pandemic is not over yet.

Web resources: "usefulness" for tourists

Navigators and routes

  • YouRoute is a website for future travel planning. Shows information about hotels, attractions, restaurants.
  • Navmii is a GPS navigator that works without an Internet connection. Contains data on traffic jams, accidents and has a built-in Google search.


Information about COVID-19

  •   is a travel planner for the US Centers for Disease Control and Prevention.
  • is a map of the world with a description of the conditions for the entry of immigrants/tourists to any country.

COVID-19 affected country map

Final Question: What is Chicago?

Life in the USA as an immigrant is full of discoveries. I realised this when I was compiling a guide to Chicago. I confess that I have not been to all the restaurants and did not know about useful sites. Now I want to try everything from morning coffee at CC Ferns to an evening cocktail at Smart Bar.

Chicago is a city of winds, skyscrapers and festivals. There are well-groomed parks, an unusual "pizza pie" and interesting museums. Tourists and expats choose what to see in Chicago, and it's enough just to walk around the center. I suggest everyone find their main attraction in the city!


Thanks for reading Chicago, Illinois travel guide: What to see & things to do in Chicago?

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