Travel in
The first impression of O’Hare International airport that struck me was its enormous size. Aircrafts often taxi for 15 minutes or so, congestion routinely delays departures and arrivals, long walks to immigration and baggage carousel, and what not. This is not an airport where one can get in and get out in double quick time. The population of Chicago is under 3 million, but the airport handles~25 times that number annually. International flights operate out of Terminal 5 while United Airlines operates domestic flights from Terminal 1. Airport Transit System connects the two terminals but it needs time. A buffer of minimum 2 hours is required if you have a connecting domestic flight.
Only Air India has a direct flight from Delhi to Chicago. I took this flight for my onward journey in 2024 but otherwise, I flew Lufthansa via Frankfurt in 2017 and British Airways via London for return journey in 2024, both out of Bengaluru. And in both the cases, transit visa was not required.
The CTA Blue Line train is the cheapest way to get to downtown area. About 45 minutes and USD 5 for a ~18 mile journey. This is a good option if you don’t have much luggage and your hotel is close to the station. Taxis may actually get into downtown faster, depending on traffic situation and costs upto US 50, including tip. Shuttle bus or Uber are also good options to get to your hotel directly.
Most international airlines operate out of O’Hare and few of them also fly to Midway International Airport which is closer to downtown area.
Where to stay
The Loop is the best place to stay. Within the Loop, I preferred a hotel closer to Riverfront during the first visit in October, 2017. Hotels closer to the riverfront are relatively more expensive but worth it for the convenience it offers. You may not find many options for budget accomodation in this area. In 2017, I could get mid range hotel rooms easily for ~USD 200 per night but the same hotels cost over USD 350 per night in September 2024.
Another good area is River North, just across the river.
In September 2024, since I had to visit nearby neighbourhoods, I stayed at Springhill suites near O’Hare airport. It was close to CTA line and offered round the clock free pick up and drop facility from/to O’hare Internatonal airport, every 30 minutes or so. It cost USD305 per night with breakfast and the room was quite spacious and comfortable. As there was a event happening in Chicago, mid range downtown hotels were all priced upwards of USD 350 per night. Few hotels offered lower rates but the room size was small, under 200 sq. ft.
Vegetarian food
Plenty of choices. You only need the google maps. A vegetarian meal in a fast food joint can be had for USD10-15 while in a mid range restaurant, it may well be upwards of USD 25 per person. You have a choice depending on your budget.
Chicago is famous for Deep Dish Pizzas and Chicago Hot Dog(with beef). Lou Malnatis is famous for its Deep dish pizza and offers couple of vegetarian options. One medium size pizza(adequate for a couple) cost USD 26. I must admit it tasted good. With beer, garlic bread and tips, I paid ~USD50 for couple.
At O’hare airport
I found better vegetarian options in the domestic terminal rather than the international one. The farmers fridge(terminal 1) was close to being a life saver, dispensing on the go vegetarian items such as pesto pasta bowl, salad, Thai noodles bowl and overnight oats. Cost ~USD 8 per item. Cold yes but honestly, who cares when one is hungry. And I could carry it to the aircraft as well. Even today, unless you have pre-booked, it is unlikely you will find any vegetarian meal options on longer duration flights in US. One outlet sold a Mexican style bowl(cold again) and a sandwich joint offered one vegetarian option with fresh toasted bread. Who said US is easy for vegetarians? As a matter of fact, egg is considered vegetarian in US.
Avoid being out late in the night
On weekdays, it does get lonely even near the waterfront area after 9PM. One evening, I had dinner near the raiIway station and decided to walk back along the river. It was just after nine and most the time, there were hardly 3-4 people around. The general advice is to avoid being out late in the night. Once the offices empty out, you will not find too many people on the streets during weekdays. On weekends, there is more crowd though.

Tipping
In US, tipping is expected. From taxis to restaurants to shuttle buses to luggage handlers, tips are expected everywhere though not mandatory. Do read available guidance though as a thumb rule, 10% of the invoice value is perhaps the minimum. Rounding off to the nearest dollar may not be enough. One big change I noticed between 2017 and 2024 is that in 2024, tips are expected even in self service joints at the time of billing, even where orders are placed and paid through Kiosks!