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Basics about the city of Chicago. It’s a world-class city with excellent food and nightlife, enjoyable summer street festivals, great museums, stunning architecture, and some of the best in entertainment and sports. Even in the freezing cold in winter, this city has something for everyone.
Getting to Chicago
Chicago is one of the best connected cities in the country. There are two major airports, the largest passenger rail hub in the Midwest, and several important highways crossing through the area.
Chicago Airports
Flying into Chicago can be done at both O’Hare International Airport and Midway International Airport. Both airports are well-connected to the city by public transportation and taxis. O’Hare is connected by the CTA Blue Line and Midway is on the CTA Orange Line.
Union Station
Union Station is where Amtrak trains enter and depart from Chicago (we came in on the Empire Builder from Seattle). Megabus services leave from Van Buren Street between South Canal and Clinton (service to Madison, Wisconsin, leaves from Jackson and Canal). Greyhound has two stations in the city center, next to Union Station and 630 W. Harrison.
Getting to and from the Suburbs
If you need to get to the suburbs, there are Pace buses, Metra trains, and NICTD South Shore trains to Northwest Indiana.
Getting Around Chicago
To get around town, the Chicago Transit Authority runs buses and trains. It’s the second largest public transportation system in the country. Click here for updated fare and pass information.
Where to Stay in Chicago
Since I’ve lived in or near the city most of my life, I haven’t had to stay at many hotels. In any case, there are plenty of options for all budgets and tastes. The best hotels are located in the Loop and Near North Side.
Sofitel
The best stay I’ve had in Chicago was at the Sofitel Chicago Magnificent Mile, which is located at Rush and Division just a couple blocks from Michigan Avenue. It includes a restaurant and bar on the property. We got an incredible rate for our anniversary so we went and spent the night there in December 2021.
The Sofitel is a luxury hotel with extremely comfortable and spacious rooms, big bathrooms, and excellent customer service. It’s also within walking distance of some of the best and most popular restaurants in Chicago. We really enjoyed our night there and had a great experience overall.
Hyatt Regency Chicago
The Hyatt Regency Chicago sits along the Chicago River and Wacker Drive. If features a restaurant, café, and bar. I stayed there for a weekend in February 2004 for a convention and to go to a Blackhawks game at the United Center. From what I remember, the hotel was very comfortable and my friend and I had an enjoyable stay. I can imagine the rooms have had significant style upgrades since then.
Eurostars Magnificent Mile
I can recommend the Eurostars Magnificent Mile (formerly Dana Hotel and Spa) in River North. It’s located on State and Erie and is a boutique luxury hotel. I stayed here for a friend’s wedding in June 2015 when it was the Dana Hotel and absolutely loved it. Rooms are very modern and comfortable.
Events in Chicago
Chicago always has something happening. For a schedule of events, nightlife, restaurant recommendations, entertainment, and more, check out Choose Chicago and TimeOut.
Chicago Sports
Sports lovers will be in heaven in Chicago. There seems to be a professional team playing just about every day of the year as well as NCAA college athletic events. The United Center hosts the Chicago Bulls NBA basketball team and the Chicago Blackhawks NHL hockey team. Soldier Field is the home of the NFL Chicago Bears. The MLS has the Chicago Fire, who also play at Soldier Field. They moved back to the city in 2020 after spending several years in suburban Bridgeview. These stadiums often host concerts as well.
We even have two Major League Baseball teams – the Chicago White Sox on the South Side at Guaranteed Rate Field and the Chicago Cubs on the North Side at historic Wrigley Field. The rivalries between baseball fans divide the city every summer (and the rest of the year, to be honest). For the record, I’m a Sox fan.
In addition to the professional teams, US Soccer often plays international friendlies and qualifiers at Soldier Field. The occasional international tournament is hosted in the city as well as club teams from Europe and Mexico playing exhibition games.
Northwestern University in suburban Evanston is the biggest in NCAA athletics, but DePaul University, University of Illinois at Chicago, Loyola University Chicago, and Chicago State University all have collegiate athletic programs for both men and women.
