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Planning the perfect 2 week USA itinerary for first time visitors

Looking  to spend 2 weeks in the USA? This post is for you. We highlight the best cities to visit across the US for first time travellers. As well as providing you with information on the best places to stay and the best things to see and do. Here is our guide to planning the perfect 2 week USA itinerary.


Before you leave on your 2 week USA trip

Before you leave on your 2 week trip to the US you need to make sure you apply for your ESTA. The ESTA stands for Electronic System for Travel Authorisation which allows entry to the USA under the Visa Waiver Programme. But this is only for certain countries such as Australia, UK and, Ireland. You will need to fill in a few questions online including your contact details, employment details, and passport information.

You also need to pay the $14 (approx) fee. Most often you will get a quick response as to whether this has been approved but sometimes it can take a few days. Mine took longer because I am a dual national so had to input two lots of passport details that needed to be checked. The ESTA is then valid for a series of multiple trips over a 2 year period. It also only allows you to stay in the USA for 90 days or less.

If you’re from a country not covered in the Visa Waiver Programme, you will need to complete a more formal process.

Tips for spending 2 weeks in the USA

2 weeks in the USA should be ample time to get a feel for the country and will allow you to visit the east and west coast. Here are some of our tips we learnt from our own trip:

  • Check what is happening in a city on the dates you plan to visit. For instance it was only after we booked flights that we realised the Chicago Marathon was happening in Chicago. This meant that hotels were booked up and super expensive. And a lot of roads were closed making it more difficult for us to get to the airport.
  • Tipping is a big thing in the USA so make sure you tip your servers and tip them well.
  • Get to grips with the city you are visiting, as there are some areas that are probably best left unvisited.
  • Also get used to tax, just because something is advertised as being a certain price this more than likely won’t include tax.
  • Laws tend to differ state by state so just be aware when travelling between them.
  • Make sure that you have travel insurance as a hospital visit will cost you a lot!
  • The USA is quite divided when it comes to politics, so it might be best to think or gauge your audience before you start rubbishing politicians.
  • Also, each US state can often feel like a different country, for instance California and New York State are not only geographically different but can often feel worlds apart in terms of culture and lifestyle.

Where to go when you have 2 weeks in the USA

If it is your first trip to the USA then you will want to visit some of the big cities. Our guide includes the following:

  • Chicago
  • San Francisco
  • Los Angeles
  • Big Bear Lake
  • Las Vegas
  • New York City

If you feel too rushed then you can always skip one of the above places. For us though, our aim was to visit as many cities as possible during our 2 weeks in the USA.

Is a 2 weeks in the USA enough time?

One of the questions you might be wondering is, is a 2 week USA itinerary enough time to see everything? Well, yes and no. For starters 2 weeks in the USA gives you ample time to explore a few major cities, and get to grips with the culture and way of life.

But you have to remember that the USA is big. Really big. Travelling between cities and states can take quite a bit of time. Whether you choose to fly or drive, you have to factor travel time into your itinerary. In an ideal world we felt like we could have spent a good 4-5 weeks alone just exploring the USA.

2 week USA itinerary in a nutshell

Day 1- Chicago

Day 2- Chicago

Day 3- Fly to San Francisco (4.5 hour flight duration)

Day 4- San Francisco

Day 5- San Francisco

Day 6- Fly to Los Angeles (1 hour flight duration)

Day 7 – Los Angeles

Day 8- Rent a car and drive to Big Bear

Day 9- Drive to Las Vegas

Day 10- Las Vegas

Day 11- Las Vegas

Day 12- Overnight flight to New York – arrive in New York AM

Day 13- New York

Day 14- New York

A more detailed 2 week USA itinerary

Days 1-2 Chicago

We flew into Chicago because we wanted to break up the long flight from the UK before heading over to the West Coast. On top of that we have both always been fascinated by Chicago’s history. From the prohibition days of Al Capone, to its incredible architecture. All in all we spent two full days in the city before flying out to San Francisco.

Some of the architecture in Chicago

Things to do in Chicago

You can read all about our two days in Chicago in detail here. But the city highlights include:

Architecture Cruise

You cannot visit Chicago without admiring the city’s incredible architecture, and an architecture cruise with First Lady Cruises is a great way to do this. The tour lasts about 1.5 hours and it is a really fascinating insight into the buildings that shaped Chicago.

Navy Pier

There is a lot to explore at Navy Pier from rides, to theatres, and restaurants. It is also a great place to go to get a fantastic view of the Chicago skyline.

The John Hancock Centre (360 Chicago)

The observation deck at the John Hancock Centre, referred to as 360 Chicago is a great place to go for those incredible views over Chicago. One of the best things though is that there is a bar, so you can sit down with a drink and take it all in.

Willis Tower (Skydeck)

Another observation point in Chicago is the Willis Tower Skydeck. The cool thing about this is that there are glass boxes built into the edge of the building. When you stand in them you feel like you are floating above Chicago. If you are short on time and can’t decide between the John Hancock Centre or the Willis Tower here is a handy article to help you.

Millennium Park

One of the most popular selfie locations in Chicago is at the Millennium Park Bean. The reflective 110 tonne sculpture is a favourite amongst tourists as you fight the crowds to get that all important selfie. Don’t miss the rest of the park including the fountains with pictures of Chicago natives that spurt water every so often.

The Chicago Bean

The Art Institute of Chicago

The Art Institute is the second largest museum in the country and is by far, one of the top things to do in Chicago. The gallery houses works from artists from Picasso to Andy Warhol.

Getting from the Airport

Once you arrive in Chicago there are a few ways to get to the downtown core. The cheapest and often quickest way to get downtown is via the L Train. The Blue Line should have you in the downtown area in approximately 45 minutes. If you are however severely jet lagged and the thought of negotiating a subway line with giant suitcases scares you (you are not alone), then the next best thing is to get the airport shuttle bus. They are slightly cheaper than a taxi and take you straight to the front door of your hotel. Just be mindful that the journey can be quite long particularly during peak hour. You can book and pay for your shuttle at one of the designated booths at the airport. The good thing as well is that you can pre book your return trip to the airport too.

Where to stay in Chicago

If you can, stay in the downtown core. Particularly on a short trip it makes it so much easier to get around in a limited time. We ended up visiting Chicago the same weekend as the Chicago marathon and so we had to book accommodation a little out of the centre. If you decide to book accommodation out of the downtown area then make sure it is close to a subway line.

Eating and drinking in Chicago

Two things that you must do when you visit Chicago are, eat a deep dish pizza and visit a speakeasy. The deep dish pizza is one of those foods that you either love or hate. We happened to love it. There are a number of places in the city that serve it and we ended up at Pizano’s. To wash the dish down, you have to visit a speakeasy. Our top recommendation is the Green Door Tavern located in the downtown area.

The Green Door Tavern in Chicago

Days 3-5 San Francisco

We left Chicago early morning and it took just over 4 hours flying time to get to San Francisco. It is important to remember that there is a time difference between Chicago and San Francisco. Chicago is actually 2 hours ahead of San Fran. By the time we landed in San Francisco it was early afternoon, so we had a good 2.5 days to spend in the city.

Things to do in San Francisco

San Francisco is a bustling hive of activity. You can read in detail about our time in the city by going here. But in the meantime here is a quick recap.

Golden Gate Park

If you want to explore some of California’s natural beauty then the Golden Gate Park is the perfect place to go. One of the highlights of the park has to be the Japanese Tea Garden which is a great place to sit and reflect if you have the time.

Golden Gate Bridge

You cannot visit San Francisco without a trip to the Golden Gate Bridge. One of our fondest memories was walking across the bridge and looking out at the San Francisco skyline. It opened in 1937 and spans the 1 mile wide straight that connects San Francisco to California’s northern counties. It is a great place to go to get photos of San Francisco’s most iconic structure.

Haight Ashbury

Haight Ashbury is a great place to go if you are a fan of the unusual. There are a number of quirky shops and cafes, and it is an area synonymous with the hippie movement in the 1960’s.


San Francisco’s Chinatown is a must for any bargain hunter. It is actually the second largest Chinatown in the USA, and bartering for goods is highly encouraged. The food around here is also really good and cheap, so do pop into one of the many restaurants if you can.


One of the best tours we have ever been on is at Alcatraz. Make sure you book your tickets in advance as if you don’t, there is a high chance you will miss out! You need to book an allocated time and the ferry will take you over to the island to explore. The audio tour here is fantastic and you do get a really good and often eerie insight into what life was like at one of the most notorious prisons in the USA.

Pier 39

Probably one of the most touristy places in San Francisco has to be Pier 39. But don’t let that put you off. It is a great place to explore, and you get some amazing views of Alcatraz from here. The sea lions are also pretty amazing to see and have been drawing tourists in for years.

Historic Cable Cars

You can’t say you have been to San Francisco if you haven’t hung off the edge of a cable car as it whizzes down one of the city’s incredibly steep hills. There are two lines, one that takes you from near Fisherman’s Wharf to Union Square and one that goes past Lombard Street.

Postcard Row

To get those postcard perfect shots of San Francisco then you have to checkout Postcard Row, famous for the row of houses called the Painted Ladies that sit with the Skyline in the background. You will probably recognise these houses from TV shows.

Lombard Street

Lombard Street is often misconceived as the steepest street in San Francisco. It is not, but it is the most beautiful. The heavily zig zagged street was designed this way as the back in the day, cars could not get up such a steep incline. These days, it is mostly tourists who drive down, although you do see the occasional resident too.

Getting from the Airport

The easiest and cheapest way to get to downtown San Francisco is via the BART, although you are limited with available downtown stops. If you are staying near Union Square then this option is perfect, but if you are staying near Fisherman’s Wharf for example you will need to disembark and change onto another form of public transport. You can also get the airport shuttle which will usually drop you straight off at your hotel.

Where to stay in San Francisco

We stayed pretty close to Union Square which was really handy. It was a short walk to Chinatown and a number of restaurants and bars. It was also close to the BART station as well as the MUNI metro.

Eating and drinking in San Francisco

Our top tip in terms of food has to be Chinatown. You have so much choice including Japanese, Chinese, and Vietnamese cuisine and it tastes really good too. It is also relatively cheap. If you are a fan of seafood we recommend heading down to Fisherman’s Wharf. They do some pretty good clam chowder bowls and quick bites.

Days 6-7  Los Angeles

If you are looking for a detailed LA guide then do checkout our post. If you are wondering how long to spend in LA we really don’t think that 2 days is anywhere near enough. For starters LA is huge. We were tempted to skip LA altogether on our trip but in hindsight we are glad we didn’t, although we would have loved to explore a lot more.

Things to do in Los Angeles

Griffith Observatory

For some great views of the Hollywood sign and LA in general the Griffith Observatory is a must. You can also learn all about the cosmos and look through some powerful telescopes.

The view of the Hollywood sign from the Griffith Observatory


You cannot go to LA without visiting Hollywood. Contrary to popular belief it is not swarming with celebrities, instead you will find your typical tourist activities and wax museums. Some must see parts are the walk of fame as well as the handprints at the TLC Chinese theatre.

Beverly Hills

This was probably one of our least favourite parts of LA. I’m sure if you have the cash to splash you might find it more enjoyable, but for us the whole place screams pretentiousness. Even Rodeo Drive has lost its pizazz. It was once an area frequented by celebrities, but with the increasing paparazzi culture and smartphones, celebrities are more reluctant to go. Nevertheless it is still an interesting place to visit just to see how the other half live.

Venice Beach

One of the true gems in LA is Venice Beach. It is one of the best places for people watching and is about as far removed from the Hollywood glitz and glamour as possible. If you do get the time we highly recommend visiting. Here are some of the best things to do in Venice Beach.

Venice Beach

Santa Monica

Just down the road (for LA) from Venice is Santa Monica. The area is slightly more upmarket than Venice Beach and is a great place to go if you like shopping. There is also an amusement park located on the pier which is great for a fun day out.

Getting from the Airport

LA is absolutely huge and so the best way to get to your hotel is via the airport shuttle. It is actually relatively cheap compared to airport shuttles in other cities, and you get dropped off right at your hotel door. You can book the shuttle at the designated booth in the arrivals section of LAX.

Where to stay in Los Angeles

There are so many different parts of LA to explore but one of the best areas to stay has to be Hollywood. There is a lot going on in terms of nightlife and it is much nicer than say Downtown LA. We actually ended up staying in Downtown LA at a nice hotel. The only issue was we didn’t really feel comfortable exploring at night so we were confined to the hotel during the evening.

Eating and drinking in Los Angeles

Hollywood is a great place to go for a mix of food. Our favourite place though was Mel’s Diner. It is a great place to go for milkshakes and apple pie, which is pretty much all I wanted since we landed in the US.

Day 8 Big Bear Lake

If you want to you could spend an extra day in LA, but we decided to take a break from the city for one night and head out to Big Bear Lake, a popular holiday destination located in the San Bernardino Valley.

Things to do in Big Bear Lake

There are so many things to do in Big Bear Lake, like hiking or hiring a boat, but for us it was all about the relaxation. It also depends on what time of the year you are planning to visit. For example in the winter months it is a popular place for skiing whereas in summer it is all about the hiking.

Getting here from LA

We hired a car in LA and drove to Big Bear Lake. It takes around 2-3 hours depending on traffic and the views along the way are absolutely stunning. If you are looking to rent a car in the US then checkout this handy guide we put together.

Where to stay in Big Bear Lake

We highly recommend booking lakeside accommodation. We stayed in a resort right on the lake where the rooms had a cabin feel. It was perfect especially in the evening as we had a fireplace which made everything feel that much cosier.

Eating and drinking in Big Bear Lake

If you make your way into the village there are a number of places to eat and drink. Our favourite though had to be the Peppercorn Grille. They do pizzas, burgers, and steak along with other things. They also rustle up a pretty decent cocktail.

Days 9-11 Las Vegas

After a relaxing night we made our way to Vegas. In our opinion Vegas is an absolute must. You literally feel like you are in another world and it is one of those places you have to see to believe.

Things to do in Las Vegas

Hotel Hopping

You would actually be surprised how long it takes to walk from one end of the vegas strip to the other, so hotel hopping in Vegas can be quite time consuming. Some of the must sees though are the Paris Hotel where you can go to the top of the Eiffel Tower. The Bellagio with its fountain show is another must see as well as the Venetian which was our personal favourite as you even had the chance to ride a Gondola.

Vegas Sign

No trip to Vegas is complete without a selfie at the Las Vegas Sign. Located at the top of the strip right near the Mandalay Bay Hotel, you will find queues of people along with the occasional bride and groom waiting to have their picture taken. The best time to go is in the morning when it is a lot quieter and you can get photos with less people.

Day trips

There are a number of day trips you can do from Vegas, including the Hoover Dam or the Grand Canyon. You can book these tours through your hotel concierge and if you have the time they are a nice break away from the craziness that is Las Vegas.

Freemont Street/ Old Las Vegas

Downtown Las Vegas, couldn’t be more different to the Vegas Strip. Nevertheless it is really worth seeing. For starters there are some of the old school casinos in Vegas such as the Golden Nugget. There is also a zip line that whizzes you across Freemont Street at speed. One of our favourite things though was the Mob Museum. It is a fascinating insight into the darker side of US history and the mob’s impact on Vegas itself. There is also the Neon Sign Museum which is where you guessed it, Neon Signs go to die. Again it gives insight into old Las Vegas and what the city was like in its heyday.

Getting from the Airport

The easiest and quickest way to get from the airport to the Vegas Strip is via shuttle bus. You may have to wait a while depending on what time you fly in, but the service is great and you get driven straight to your hotel door.

Where to stay in Las Vegas

Ideally you want to stay on the Vegas Strip as this is where most of the action is. We stayed at Paris, and it was centrally located and in the middle of all the action. Hotels in Vegas range in price and also standard so whatever your budget, you will be spoilt for choice.

Eating and drinking in Las Vegas

You will also be spoilt for choice for food and drink in Vegas, from the elaborate hotel buffets to the restaurants owned by celebrity chefs. There are way too many places to choose from and something to cater to all tastes.

Days 12-14 New York

The final city that we highly recommend on any trip to the US is New York. It really is one of the most incredible places we have visited and there is so much to see and do. We ended up getting a red eye flight from Vegas into New York that saved us a nights accommodation and meant we had an extra full day to spend in New York.

Things to do in New York

New York is epic and there is probably enough to do for months on end, but we have listed some of the highlights and must sees to help you plan your itinerary. We also have a guide if it just so happens to rain during your time in NYC. 

Central Park

Central Park was a must for us especially because we had seen it so many times in the movies or on TV. The Park is a bustling hive of activity with rollerbladers, bikes, and tourists travelling in horse and carts. Some highlights in Central Park include the boathouse where you can rent a row boat particularly in those summer months with the skyscrapers in the background. Another must is the Lennon memorial titled Strawberry Fields.  It is located adjacent to the Dakota Building, which is where John Lennon was living when he was shot returning home on the 8th of December 1980.

Brooklyn Bridge

One of the most iconic structures in New York has to be the Brooklyn Bridge. And taking the walk across is a must do when visiting the city.

Empire State Building

The Empire State Building is probably one of the most well recognised buildings in New York. Located on 5th Avenue, the Empire State is a 102 story art deco style building. Construction on the building began in 1930 and doors opened in 1931, a mere 13 and a half months after the first beam was laid. You get some awesome views of New York from the 86th floor of the building, just be prepared to be pushed around by crowds of tourists.

Top of the Rock

The Rockefeller centre was created by J.D. Rockefeller Jr, and was designed to be a city within a city. Building was completed in 1933 and since then the building has become a cultural hub.You will get to see the city from the 67th, 69th and 70th floors and like the Empire State the views are incredible. It is generally not too crowded on the observation decks. Plus the cool thing is you can get a picture of the iconic Empire State Building as well.

If you are tossing up between the Empire State and Top of the Rock here is a handy guide to help you decide which one to visit.

The High Line

The High Line is a 1.45 mile elevated park on a disused train track and is a garden oasis in the middle of a busy city. It is a lovely place to go for a walk or just sit down and take in your surroundings.

Statue of Liberty

Another New York City icon is of course the Statue of Liberty. To see the Statue up close you can book a boat tour that takes you to Liberty Island and Ellis Island. If you are planning to do this you should set a full day aside and book in advance. It is super busy and you will spend a lot of the day just waiting in line. We were short of time so we only managed to see Liberty Island to get a few close up shots of the Statue. It is a wonderful experience and we would really recommend it. Alternatively you could get the Staten Island Ferry for a glimpse of Lady Liberty herself, but you certainly don’t get as close as you do on the tourist boats.


New York has some pretty amazing museums, from the Natural History Museum to the Guggenheim. We decided to visit the Museum of Modern Art which houses works from artists such a Van Gogh, Dali, and my personal favourite Andy Warhol. You seriously cannot go to New York without visiting at least one museum.

Getting from the Airport

There are a number of airports in New York, and most of them have a shuttle bus that will take you straight to your hotel. Just be mindful that New York traffic can be pretty bad. But ultimately it is cheaper than a taxi which is handy.

Where to stay in New York

We ended up staying near Times Square which was great on a short trip, but if you are visiting for a bit longer, we recommend staying in one of the neighbourhoods like the East Village for example. There is a lot more atmosphere and you get to see the less touristy side of New York. No matter where you stay though you really want to make sure you are near a subway station which will make getting around New York so much easier.

Eating and drinking in New York

We actually write a post all about the foods you need to try in New York. There is so much choice and it is hard to narrow down. There are some great places to eat and drink in the East Village including our favourite, a 24 hour Ukrainian dinner called Veselka, it is also a great place for drinks and one of our favourite bars was The Immigrant. Another must is a visit to the Dominque Ansel Bakery which is of course the home of the famous Cronut.

2 weeks in the USA itinerary recap

Hopefully this 2 week USA itinerary has you all excited about booking your trip to the USA. There are so many other cities to visit though and you can check out our East Coast and West Coast itinerary to cover more places you should visit.

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  • Merilyn
    May 27, 2019 at 4:26 am

    How much does it cost?

    • Lizzie
      June 9, 2019 at 5:04 pm

      Hi, so we probably spent around $1800 on accommodation and had about $2000 of spending money between the two of us. We picked mid market accommodation that was always central so you could probably bring this down a bit. We did spend quite a bit on attractions particularly in NYC so I guess it depends on what you plan to see and do as well. I hope that helps.