For a first trip, I’d start with The Loop or River North. But they aren’t necessarily the best choices for a holiday built around restaurants, family time or baseball. Here are five areas and the hotels I recommend, so you can choose based on the part of Chicago you most want close by.

The Best Areas in Chicago

• The Loop - best area for first-time visitors
• River North - best area for restaurants and nights out
• Streeterville - best area for families, shopping and the lake
• West Loop and Fulton Market - best area for food and a grown-up trip
• Lakeview and Wrigleyville - best area for baseball and a local neighbourhood feel

Below, I’ll take you through the areas and recommend hotels at different price points and with different strengths. You’ll also get help weighing up the transport, a hotel’s exact location and how the neighbourhoods differ in the evening.

1. The Loop - best area for first-time visitors

• Distance from the centre: You’ll be staying in central Chicago, south of the Chicago River and close to several of the big sights.
• Transport: Several CTA train lines meet in the area. The Blue Line runs to O’Hare, while the Orange Line connects the centre with Midway.
• Time from the airport: The Blue Line normally takes 40 to 45 minutes from O’Hare to downtown. From Midway, the Orange Line takes around 25 minutes. Then add the journey to your hotel.
• Price range: $$ to $$$. A riverside location and a view often cost extra.
• Safety: Keep track of your phone and bag at stations. Choose well-lit routes home, especially on the quieter office streets.

The Loop is my most straightforward recommendation for a first trip with sightseeing on the agenda. You’ll be staying among the office towers, by the elevated railway and close to some of the city’s best-known parks and museums. You can spend several days on things nearby without starting every morning with a long journey across the city.

I’d look at the eastern or northern part in particular if you want Millennium Park, the Art Institute and the river close by. An address further south or west can be just as handy for trains and certain sights, but it gives you a different walk home. So look at the street the hotel is on, not just the word downtown.

The CTA’s airport guide shows the connections from both O’Hare and Midway. The Blue Line from O’Hare is especially useful when traffic into the centre is heavy. I’d normally wait to pick up a hire car until the trip continues out of Chicago, as hotel parking in the centre can be an expensive way to store a car.

See hotels in The Loop here.

The area suits a stay of three or four nights with parks, a museum, a boat tour and trips into other neighbourhoods. You don’t need to stay right next to everything, but a good train connection gives you freedom. I’d also check where your room is if the hotel sits close to the elevated tracks, as train noise can be part of the stay.

The downside of parts of The Loop is that the office streets go quiet once the working day is over. It’s less of an obvious pick if you’re dreaming of a wide selection of bars right outside the door every evening. For that kind of trip, I’d compare it with River North or the West Loop, even though your daytime outings will then take a little more travelling.

If you’re planning several big-city stops in the USA, my guide to where to stay in New York can help with the next choice. In Chicago, I’d prioritise a good address over one more hotel deal far from the centre. On a short trip, the time you save every day is part of what you’re paying for.

Places to Stay in The Loop

The LaSalle Chicago - luxury choice in the central part of The Loop

The LaSalle is my pricier pick if you’d like to combine a central base with a more polished hotel experience. The hotel has a gym, a lounge and a bar, so it also works for a calm start or end to the day.

I’d consider it especially for couples who like to spend time at the hotel between outings in the city. A previous guest highlights how helpful the staff are. You’re paying for more than a bed close to the train here, so choose it when the hotel itself is genuinely part of the holiday.

One guest writes on Booking.com: “The staff were very friendly and helpful.”

See photos and book The LaSalle Chicago here.

L7 Chicago by LOTTE - spacious rooms close to the river

L7 sits by the Chicago River and has a gym that’s open around the clock. It’s my suggestion if you want the northern part of The Loop as your base and an easy walk across the river to River North.

One guest highlights large, clean rooms and nice decor. I’d compare it with the hotels on the other side of the river if space and location matter more than staying in a particular neighbourhood. If the view is what matters for your stay, book a view category specifically.

One previous guest points out: “The rooms are large, clean and new, with nice decor.”

See photos and book L7 Chicago by LOTTE here.

Club Quarters Hotel Central Loop - practical city hotel by the trains and Willis Tower

Club Quarters is in the central part of The Loop, within walking distance of Quincy station and Willis Tower. The hotel has a restaurant and a pub, and I’d look here in particular for a trip where you’re out for most of the day.

It’s a simpler set of priorities than a luxury hotel: a central address, a good bed and easy access to transport. A previous guest highlights exactly that bed, along with a clean, quiet room. Compare the actual room size if you’re bringing a lot of luggage.

One guest review on Booking.com reads: “The bed was very comfortable.”

See photos and book Club Quarters Hotel Central Loop here.

2. River North - best area for restaurants and nights out

• Distance from the centre: The area lies north of the Chicago River, directly across from The Loop. You’re still centrally placed for sightseeing.
• Transport: The Red Line and the Brown Line are the ones to look at, depending on the address. You can also walk across the bridges to The Loop.
• Time from the airport: Allow around 35 to 70 minutes by car from O’Hare, longer in heavy traffic. By train, you’ll need a walk or a change once you reach downtown.
• Price range: $$ to $$$. You’ll find both ordinary city hotels and some of Chicago’s most expensive hotel addresses here.
• Safety: Look after your valuables around bars and busy stations. Arrange transport home if you end up far from your hotel late in the evening.

River North is the area I’d choose if restaurants and nights out matter just as much as the daytime sights. You’re still central, but you’ve got plenty of places to eat and drink in the streets north of the river. That makes it easier to find dinner close to your hotel after a long day in the city.

The location is especially good for couples and friends on a short city break. You can walk down to the river, cross into The Loop or head for the shops on Michigan Avenue. I’d prioritise the southern and eastern part of River North if you’d like to combine all three without needing transport for every outing.

An architecture boat tour is a good way to get your bearings from this part of the centre. The Chicago Architecture Center’s river cruise focuses on the buildings along the river. I’d set aside time for it early in your stay and then go back to the places that caught your interest.

See hotels in River North here.

The neighbourhood is bigger than the streets right by the water, though. A hotel further west doesn’t put you as close to Michigan Avenue and the lake. Compare the address with the restaurants and sights you already know you want to visit. A great view from a single corner room isn’t in itself a good location for the whole stay.

The biggest drawback is noise on the livelier restaurant and bar streets. I’d happily pay for a location here, but I’d ask for a room away from the street if a good night’s sleep is a priority. For a family who mainly want to spend their days by the lake and at Navy Pier, Streeterville can be a better compromise.

You can easily have a great trip without choosing one of the most expensive hotels. River North also has more ordinary hotels where the central address is the main advantage. I’d compare the total price including breakfast and any mandatory fees, and keep some of the budget for the restaurant visits that make this neighbourhood worth choosing.

Places to Stay in River North

The Langham Chicago - luxury hotel by the river

The Langham is in a building designed by Mies van der Rohe, close to the Chicago River and Michigan Avenue. It’s my pick when you want architecture, location and the hotel stay itself to be a big part of the trip.

A previous guest highlights the bar and being able to use the gym. I’d pay for The Langham above all on a trip with time to actually be at the hotel. For a packed sightseeing schedule the location is still good, but you’ll get less out of the difference compared with a simpler hotel.

One guest describes their stay like this: “The bar experience was really good.”

See photos and book The Langham Chicago here.

Eurostars Magnificent Mile - modern hotel close to shopping and restaurants

Eurostars is around a five-minute walk from the shops on the Magnificent Mile and has modern rooms. It’s my alternative if you want to combine River North’s restaurants with a location close to Michigan Avenue.

One guest who stayed in a panoramic room highlights the view as well as the bed and pillows. You need to book the right category to get that view. I’d compare the hotel on location and room type, and I wouldn’t assume every room has the same outlook over the city.

One previous guest writes on Booking.com: “The bed and pillows are very comfortable.”

See photos and book Eurostars Magnificent Mile here.

Hampton Inn & Suites Chicago-Downtown - practical base for a longer city stay

Hampton Inn & Suites is a more no-frills choice in River North, with a gym and a central location. I’d put it on the shortlist for a stay of several nights, when a room that works well and a short walk to restaurants count for more than a grand hotel experience.

A previous guest describes the room as large and very clean. Choose between the specific rooms and suites based on how much space you need. It’s especially relevant if you’d like to stay in this area and still keep some of the budget free for sights and dinners.

One guest writes on Booking.com: “The room was large and very clean.”

See photos and book Hampton Inn & Suites Chicago-Downtown here.

3. Streeterville - best area for families, shopping and the lake

• Distance from the centre: You’ll be staying east of the Magnificent Mile and north of the river, with Lake Michigan and Navy Pier to the east.
• Transport: Buses and walking are the practical ways to reach the lake. The nearest train stations are to the west, so even a central address can mean a walk to the train.
• Time from the airport: Allow around 35 to 70 minutes by car from O’Hare. If you take the train to downtown, there’s normally a further stretch to cover before you reach your hotel.
• Price range: $$ to $$$. Many larger hotels and suites are close to the shops and the lake.
• Safety: Follow the swimming flags and instructions at the beach. On the lakefront paths, watch out for cyclists and other path users.

Streeterville is my suggestion if you want to combine the big city with walks by the lake and an easy schedule for the family. You’re staying between the Magnificent Mile and Lake Michigan, so shopping, restaurants and the water can all be part of the same day. It’s still a central hotel base, but with a different focus from The Loop.

I’d consider the neighbourhood especially in summer, when the lakefront takes up more of your plans. You can take a morning walk along the water and head back to the hotel before your next outing of the day. Choose a hotel in the western part and the shops and trains are closer, while further east the lake plays a bigger part in your days.

Navy Pier’s visitor information shows what you can do on the pier and how to get out there. Navy Pier itself is open to the public, while the individual attractions may require a ticket. I’d plan it as part of a day by the water, and I wouldn’t let it decide your whole choice of hotel.

See hotels in Streeterville here.

For families, a suite with kitchen facilities can be a big advantage here. You can have a simple breakfast and take a break without having to find yet another restaurant. Compare the actual number of beds at the same time, as more floor space doesn’t help much if everyone still has to share a sofa bed.

The downside is that several hotels are some way from the train, even though they look central on the map. You’ll notice that with suitcases from the airport. I’d look at the last part of the route and perhaps take a taxi for that stretch. An address close to the lake can also feel more exposed to the wind on cold days, so the time of year makes a difference.

Streeterville suits three or four nights with a mix of museums, shopping and time outdoors. If you’re travelling on to California, my guide to where to stay in Los Angeles can help with the next city. In Chicago, on the other hand, you can often do without a car and get around on foot, by bus and by train.

Places to Stay in Streeterville

Riu Plaza Chicago - larger city hotel close to the Magnificent Mile

Riu Plaza has a gym, a terrace and a bar, and it’s within walking distance of Ohio Street Beach. It’s my pick if you’d like to combine the shops and the lake with a larger hotel that also has places to spend time outside your room.

One guest who travelled with their child highlights the space in the room and the daily cleaning. I’d compare the specific family set-up and the price of breakfast with a suite in the area. The location is especially appealing when both shopping and walks by the water are on the agenda.

One previous guest points out: “The room was very spacious.”

See photos and book Riu Plaza Chicago here.

Ivy Boutique Hotel - smaller hotel close to the shops

Ivy is two blocks from the Magnificent Mile and has spacious rooms with large windows. It’s my alternative for couples who’d like to stay centrally in Streeterville and prefer a smaller hotel to a big conference hotel.

A previous guest highlights how much you can reach on foot. I’d choose the hotel for the way the rooms are furnished and for its location by the shops. For a family who need a kitchen and several separate places to sleep, I’d also look at the all-suite hotels before booking.

One guest review on Booking.com reads: “Everything was within walking distance.”

See photos and book Ivy Boutique Hotel here.

Sonesta ES Suites Chicago Downtown Magnificent Mile Medical - suites with kitchens for a stay of several nights

Sonesta ES Suites has suites with kitchens and a gym. It’s my practical pick when you’d like a base for several nights and the option of making a simple breakfast or a light meal yourself.

A previous guest describes the hotel as comfortable without calling it luxurious. That’s also how I’d judge it: on space, layout and the total price for the family. Check the room category so the kitchen and bed arrangement match what you expect.

One guest describes their stay like this: “Not luxurious, but very comfortable.”

See photos and book Sonesta ES Suites Chicago Downtown Magnificent Mile Medical here.

4. West Loop and Fulton Market - best area for food and a grown-up trip

• Distance from the centre: The area lies west of The Loop. Fulton Market and Randolph Street are good reference points for restaurants and hotels.
• Transport: The Green Line and the Pink Line serve Morgan station. The Blue Line is the one to look at further south, depending on the hotel’s address.
• Time from the airport: Allow around 30 to 60 minutes by car from O’Hare, longer at rush hour. The train journey and the final walk vary by hotel.
• Price range: $$ to $$$. Popular boutique hotels and restaurant weekends can be expensive.
• Safety: Stick to the busy streets and a well-lit route home. A hotel far to the west can have different surroundings from Fulton Market.

The West Loop is the first place I’d look if eating well is one of your reasons for travelling to Chicago. Around Randolph Street and Fulton Market in particular, restaurants and bars sit close together, so you can spend the evening near your hotel. It’s a good choice for couples or friends who put dinner high on the list.

The former industrial and warehouse buildings give the area a different character from the skyscrapers by the river. The official guide to the West Loop covers Restaurant Row and Fulton Market, among other things. I’d choose a hotel close to those streets if the restaurants are what you’re coming for, and book tables well in advance at the places that matter most.

The area is also appealing when you’ve been to Chicago before and would like to stay somewhere other than the classic sightseeing base. You can spend the morning in the centre and come back to the neighbourhood in the afternoon. A slightly longer trip to Millennium Park is easier to accept when your evenings are easy and enjoyable in return.

See hotels in West Loop and Fulton Market here.

I wouldn’t treat the West Loop as one precise location, though. Hotel addresses towards the United Center further west give you a different base from those by Fulton Market. For a concert or a game that can be an advantage, but for the restaurant streets you need to check the actual distance. The neighbourhood name a hotel uses doesn’t tell the whole story.

The downside is that you’re further from the lake and from several of the places first-time visitors want to see. You need to be prepared to take a train, bus or taxi for some outings. A hotel with great design is only a good choice if the location fits your plans. Otherwise I’d sooner pay for a more central address.

For a weekend with two good dinners and a couple of bigger sights, I’d happily stay here. On a longer stay, a suite with breakfast can be a more practical choice than the most striking boutique hotel. Compare the two types, and decide how much of your holiday budget you want to spend on the room and how much should be left for the restaurants.

Places to Stay in West Loop and Fulton Market

Nobu Hotel Chicago - luxury choice in the middle of the restaurant district

Nobu is my pricier pick in the West Loop if you’d like the hotel’s design and atmosphere to be part of the trip. The hotel has a bar and is well placed for the restaurant area, so you can spend the evening close to your base.

A previous guest highlights the style and the overall feel of the hotel. I’d look here in particular for a trip for two with time to enjoy the place. For a stay where you just need somewhere to sleep between long days of sightseeing, a simpler hotel can leave more room in the restaurant budget.

One previous guest writes on Booking.com: “The style and the people.”

See photos and book Nobu Hotel Chicago here.

The Emily Hotel - modern hotel with a rooftop lounge in the West Loop

The Emily has a restaurant, a rooftop lounge and a garden, and it sits among the West Loop’s restaurants. It’s my alternative if you’d like a hotel with places to unwind after the day’s outings but still want to spend your evenings out in the neighbourhood.

A previous guest describes the room as very clean and quiet. That makes the hotel worth comparing if you want to stay close to the action and still prioritise a good base to come back to. Look at where the room is, as evenings in the neighbourhood can be lively.

One guest writes on Booking.com: “The room was very clean and quiet.”

See photos and book The Emily Hotel here.

Homewood Suites Chicago West Loop - suites and breakfast for a longer stay

Homewood Suites is an all-suite hotel with a hot breakfast included, according to the description on Booking.com. It’s my more practical pick when you want to stay in the West Loop and would like a little more space around you.

One guest highlights how close it is to lots of restaurants. I’d compare it especially for a stay of several nights, when you’ll use an easy morning routine and a larger room every day. You’re choosing a different kind of hotel experience from Nobu and The Emily, but you can still enjoy the neighbourhood’s evenings.

One previous guest points out: “Location close to lots of restaurants.”

See photos and book Homewood Suites Chicago West Loop here.

5. Lakeview and Wrigleyville - best area for baseball and a local neighbourhood feel

• Distance from the centre: Lakeview is north of the centre, around 7 to 9 kilometres from The Loop depending on the hotel.
• Transport: The Red Line connects the area with downtown. Choose your hotel by the walking distance to stations such as Belmont or Addison.
• Time from the airport: Allow around 30 to 60 minutes by car from O’Hare. By train, you’ll normally need a change or an extra local connection.
• Price range: $ to $$$. Prices close to Wrigley Field can rise sharply on game and concert days.
• Safety: Keep an eye on your bags in the crowds around the stadium, and expect busy trains before and after big events.

Lakeview is my suggestion if you’d like to stay in a neighbourhood with residential streets, cafés and everyday life, and head into downtown when you need to. Wrigleyville is the part around Wrigley Field, where baseball and bars play a bigger role. The two moods sit close together, but you should pick your street based on the holiday you want.

For a Cubs game, a hotel near the stadium is hard to beat for convenience. You can walk to the game and stay in the area afterwards without having to join the worst of the queues for transport. If you’re travelling with no interest in baseball, I’d check the events calendar instead, so a high hotel price and a noisy evening don’t come as a surprise.

The city’s official Lakeview guide shows the differences between Wrigleyville, East Lakeview and the Southport Corridor, among others. I’d happily stay here for four or five nights, when there’s also time for a morning coffee in the neighbourhood and trips to the lakefront. For a single night of classic sightseeing, I’d choose somewhere more central.

See hotels in Lakeview and Wrigleyville here.

You can also head for Lincoln Park further south and spend a day in greener surroundings. Lincoln Park Zoo has free admission and is an obvious stop with children. Your hotel’s address decides whether it’s a reasonable walk or a bus ride, though, so plan by the map and not by the neighbourhood name alone.

The biggest drawback is the travel time to the museums and sights around The Loop. The Red Line is useful, but an address far from the station adds extra minutes to every journey. I’d make that connection a priority, especially without a car. Choosing a cheap hotel far from both the train and the sights can make a short city break harder work than it needs to be.

In return, you can get a pleasant base with restaurants and a different rhythm from the office district. If your holiday continues south, my guide to where to stay in Miami offers a completely different take on an American city break. In Lakeview, I’d choose a hotel based on the neighbourhood’s everyday life, how close it is to the train and any evenings you’ve planned at the stadium.

Places to Stay in Lakeview and Wrigleyville

Hotel Zachary - best location for a game at Wrigley Field

Hotel Zachary is directly across from Wrigley Field and has its own restaurant. It’s my clear pick if baseball is one of your main reasons for choosing Lakeview and you’d like to be able to walk straight back to the hotel after the game.

A previous guest highlights exactly that location across from the stadium. I’d pay more for it on a trip built around a game or a concert. On other trips, compare the price with hotels in the quieter parts of the neighbourhood, where the stadium address isn’t the whole point.

One guest review on Booking.com reads: “Right across from Wrigley Field.”

See photos and book Hotel Zachary here.

Best Western Plus Hawthorne Terrace - classic hotel in Lakeview with a hot tub

Hawthorne Terrace is in Lakeview, within walking distance of Wrigley Field and the Red Line. The hotel has a glass-enclosed hot tub, which makes it appealing if you’d also like to be able to relax on site after a day in the city.

A previous guest highlights the breakfast and a clean room. I’d choose the hotel as a base for several sides of the neighbourhood, not just for a single game. Check the distance to the station and the breakfast terms for the specific offer when you compare it with other hotels.

One guest describes their stay like this: “The breakfast was really good.”

See photos and book Best Western Plus Hawthorne Terrace here.

Majestic Hotel - smaller, historic hotel in the neighbourhood

Majestic is a historic hotel in Lakeview near Wrigley Field. It’s my alternative if you’d prefer a smaller hotel base to a big address in the middle of the centre and you’d like to spend time in the neighbourhood’s streets.

A previous guest highlights a spacious room and a pleasant shared lounge. I’d look here for a stay where morning coffee, restaurants and trips by train are part of the holiday. Choose by the specific room type, as older hotels can have rooms laid out in different ways.

One previous guest writes on Booking.com: “The room was spacious and comfortable.”

See photos and book Majestic Hotel here.

Where should you avoid staying in Chicago?

I’d normally rule out a hotel by O’Hare or in Rosemont for a short sightseeing trip. It can make sense before an early flight or for a particular event, but the daily journey into Chicago eats up a big part of the time you could otherwise have in the city.

Also look closely at hotels that use downtown or West Loop very loosely. An address far from the train and the places you want to visit doesn’t become practical because of the name alone. I wouldn’t label the whole of the south or west of Chicago as areas to avoid. For a first trip, the choice here comes down to good connections, a simple route home and being close to what you’ve planned.

For a first trip, I’d start with The Loop and River North. The Loop is the easy base for classic sightseeing, while River North is a better fit for a trip with lots of evenings out at restaurants. I’d choose Streeterville above all for the family, for shopping and for days when you want the lake close by.

The West Loop is my suggestion for a holiday where dinner is part of the main event. Lakeview gives you more neighbourhood life and the easiest base for Wrigley Field, but it means more travelling to the centre. None of the five areas is best for every trip, so choose by the things you want to spend most time on.

I’d set aside at least three nights for Chicago, and ideally one more if you also want time for a game, several museums or trips out into the neighbourhoods. Compare the hotel’s total price, the size of the room and the final walk from the train. A good address makes it easier to enjoy the city at a pace where you also get time to sit by the river.

If Chicago is one stop on a longer trip around the USA, I’ve also written guides to where to stay in Boston, where to stay in San Francisco and where to stay in Orlando, so you can plan the next cities in the same way.

The post Where to Stay in Chicago? The 5 Best Areas & Places to Stay appeared first on Destination Well Known.