Flying to Chicago
Chicago has two airports–O’Hare (ORD) and Midway (MDW). Both airports offer convenient service to downtown Chicago (“the Loop”) via the subway. For a great series of maps and general information, check out https://wikitravel.org/en/Chicago.
O’Hare is the larger of the two airports and is served by United, American Airlines, Delta, Spirit, Frontier, and Alaska. From O’Hare, take the Blue line to downtown Chicago (about 45 min ride) and it costs $5. Uber/Lyft is about $30-$50 one way and can take 30-60 minutes depending on traffic. Taxi service is usually $50-$70 one way.
Midway is primarily served by Southwest and Delta. From Midway, take the Orange line to downtown Chicago (about 25 min ride) and costs $2.25. Uber/Lyft is about $25-$45 one way and can take 20-40 minutes depending on traffic. Taxi service is usually around $30-$50 one way.
Getting around Chicago
Taking the train from the airport hands down is going to save money and be just as fast as getting a car–sometimes faster. At each airport there is only one CTA train and it only goes in one direction, so it’s not hard to figure out.
Once you’re at your hotel, we strongly recommend using Uber or Lyft if you are not used to big cities. Both are easy to use and safe. The drivers are very used to dealing with tourists.
If you are used to taking the bus or the subway, Chicago has you covered. The express bus system is very good if it’s going your way. Google Maps provides fine transit directions but the best app for transit is Citymapper (for iPhone or Android). Each ride is $2.25 except from O’Hare where it’s $5. You can use Apple Pay, Google Pay, Samsung Pay, and contactless credit cards to get on board.
We also have an excellent and fun bikeshare system called Divvy. You’ll see the Chicago-blue Divvy bikes all over town. A 24-hour pass costs $15 and a single ride costs just $3. This is a great alternative to getting into a car and lets you see more of the city at your own pace.
Please: don’t drive in Chicago–don’t rent a car. Guys, it’s not fun and it’s not worth it. Our city has excellent public transit, and you can get an Uber or Lyft car at the push of a button. Renting a car just means trying to figure out how to park it. We strongly recommend you not drive to the city or in the city.
The day of the wedding: We figure most people will take an Uber or Lyft ride from their hotel direct to the venue. If staying in the Loop or Magnificent Mile, expect to pay about $15-20. If you’re in the Loop, you can also take the Brown Line to the Montrose station–cost is just $2.25.
Good areas to stay
Most visitors to the city prefer staying in two main areas: the Loop and the Magnificent Mile. The Loop is at the center of town and is named for the continuous loop of elevated trains that surround it. The Loop has more of the business district and it is adjacent to famous landmarks like “the Bean” and the Art Institute. The Magnificent Mile, which is a stretch of Michigan Avenue just north of the Loop, has luxury shopping and the fabled Chicago Water Tower. Either place is a fine option, although the Mag Mile can be a little more expensive.
Some suggested hotels
Chicago is full of hotels for every price range, style, and location.
Some guests have found good luck and more reasonable prices at The Cambria and the ACME Hotel. We can’t vouch for these. We have visited the Ace Hotel and it is a super cool spot. We are also comfortable at the W Lakeshore (it’s a little pricey).
Also, John and Paula Pisarski were nice enough to vet a few hotels in the Loop/Downtown Chicago. The following hotels come with the John and Paula Seal of Approval!
Embassy Suites Magnificent Mile – Moderate (Pisarski family HQ)
511 North Columbus Dr.
Chicago IL 60611
Homewood Suites / Hampton Inn – Moderate
152 E. Huron St
Chicago IL 60611
London House Chicago – Full Service (Hilton property)
85 East Wacker Dr.
Chicago IL 60601
The Palmer House – Full Service (Hilton property)
17 E. Monroe St
Chicago IL 60603