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How to Spend $10,000 on a Vacation in Chicago

By: Ashley Akridge

Edited By: Scott Sidders

Updated on November 6, 2023

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If you're visiting Chicago and have $10,000 to spend on a vacation, here are the best ways to spend that money. There are many options, from staying in a luxurious hotel to visiting the best museums.

Chicago is a fascinating city. Whether you are going for business or pleasure, Chicago is a city that has a lot to offer. It's not the most expensive city in the world, but you will still need to budget your spending well to make sure you get the maximum experience out of it. Here's how to do it right.

How much does a vacation in Chicago cost? With these simple tips and our recommended places, you will be able to enjoy the city of Chicago with your family and friends.

What can you get for $10,000 in Chicago?

Chicago skyline aerial view, Illinois, USA

Hotel - $1,200
Airfare - $800
Food and drink - $1,200
Shopping - $1,000
Miscellaneous - $1,500
Entertainment and sightseeing - $2,300

Airfare to Chicago

This is the only trip-related expense that's tough to estimate, because we don't know which city you'll be flying from. But it doesn't matter much, because the typical round-trip ticket to Chicago from anywhere in the U.S. costs $400 or less, including taxes. Even if you're flying internationally, you only need to pay a few hundred dollars more than that.


Where to Stay in Chicago

Chicago skyline aerial sunset view

Here in Chicago, we're fortunate to have excellent accommodations for every budget and a wide array of things to see and do no matter the time of year. So whether you have $10,000 or $100,000 to spend on travel, spending it here should be seriously considered. If you can spare a little more for your trip, check out our list of luxury hotel recommendations for Chicago for even greater luxury.

InterContinental Chicago Magnificent Mile

If you're looking for luxury accommodations with world-class views of Lake Michigan, the Windy City and Navy Pier, the InterContinental Chicago Magnificent Mile is a luxurious place to stay. Located on the historic Magnificent Mile, this hotel has been around for almost 100 years and features stunning art deco architecture.

The hotel has hosted a number of celebrities, from the Rolling Stones to Madonna to U2. The on-site restaurant, Michael Jordan's Steak House, is considered one of the best steakhouses in Chicago. Other amenities include a fitness center, indoor swimming pool and business center. If you want to relax after a long day of sightseeing, the InterContinental Chicago Magnificent Mile has some of the best places in the city. ENO Wine Bar has an excellent selection of cheese, charcuterie, and wine. Godiva Chocolatier offers decadent treats that are too good to pass up!

Kinzie Hotel

If you're going with a large group of friends or family members (or both), consider staying at the Kinzie Hotel. It has suites that sleep 2-8 people, so if you've got a large group and want to stay together, this is the place. The hotel itself is centrally located in River North. It's near the Magnificent Mile and Millennium Park, as well as some great restaurants in River North and the Gold Coast.

LondonHouse Hotel

The LondonHouse hotel is a great choice for luxury travelers. It has a rooftop bar with spectacular views of the Chicago River and Lake Michigan; luxurious rooms with flat-screen TVs and marble bathrooms; and a spa on site. Rooms start at $159 per night, which comes out to $1,113 for an 7-night stay. A person who has a budget of $10,000 for vacation in Chicago can stay at the LondonHouse Hotel and enjoy a lavish vacation.

Where to Eat in Chicago

Deep Dish Chicago Style Pizza

When it comes to food, Chicago does it best. Home to some of the country's most acclaimed restaurants, the city boasts an incredible array of dining options. From Michelin-starred establishments to neighborhood favorites, here are some of our top picks for where to eat in Chicago. These are the 6 best restaurants in Chicago right now.

Tillman's Roadhouse

Tillman's Roadhouse has the perfect blend of down-home Chicago-style cooking and a hip, low-key vibe. The food is as much a part of the city's fabric as the Wrigley Building — think succulent chicken wings, hearty burgers and inventive twists on classic fare. The fun atmosphere makes this spot a favorite for weekend brunch with friends or for special occasions.

Girl and the Goat

This restaurant is one of the most popular restaurants in Chicago right now (and for good reason). The food is delicious and creative, drawing inspiration from all over the world with an emphasis on local ingredients. The menu changes often based on what's fresh and in season, so there's always something new to try every time you go. If you have trouble deciding what to order, we recommend getting their tasting menu. It gives you a little bit of everything!


This three-Michelin-starred restaurant is ranked No. 7 on the World's 50 Best Restaurants list and is one of only 13 restaurants in North America to earn a Michelin Guide three-star rating. Led by chef Grant Achatz,

Alinea presents a 20-plus-course tasting menu that changes four times per year and focuses on innovative, hyper seasonal cooking techniques and presentations. The restaurant is also known for its hands-on service style that fully immerses guests in the dining experience — servers will pour water directly into your mouth or present ingredients tableside so you can smell them before they're incorporated into your meal.

Longman and Eagle

This gastropub has incredible food that will blow you away (especially if you're a meat lover). One of their most popular dishes is called "Bucket O' Chicken," which comes with 5 different types of fried chicken wings served with 7 different types of dipping sauces. Definitely make sure you get an appetizer here – they have some really good ones!

Aloha Ramen

Aloha Ramen is a welcome respite for those in Chinatown craving comfort food, particularly late at night. Aloha Ramen prides itself on its variety of broths and noodles, allowing guests to choose their favorite combination of the two — whether it's chicken, pork belly or tofu. On top of that, they also offer add-ons such as soft-boiled eggs and corn.

The Purple Pig

The Purple Pig is a Mediterranean restaurant that offers a variety of wines and a fine dining experience with an extensive menu that focuses on sharing plates, fresh flavors, and wine pairings. Home to the best olives in Chicago, it's a place you can enjoy authentic Greek cuisine while relaxing by the fireplace or in the lounge.

Chicago Pizza Tour

Have you ever tried a pizza in Chicago? There's no doubt that the Windy City is one of the best places for this delicious dish, but it can be hard to find the perfect slice. That's why you should join a Chicago Pizza Tour. You get to go on a bus guided neighborhood tour and try as many different types of pizza as your stomach can handle. Yum!

Where to Drink in Chicago

Wine glasses on a rooftop in Chicago

Maude's Liquor Bar

This French restaurant offers a whimsical atmosphere and a menu that changes every month. Sample this truffle potato salad or this roasted duck breast while enjoying craft cocktails.


Scofflaw is a craft cocktail bar that has brought the speakeasy experience to Chicago. Book a table at this Chinatown restaurant, and order some oysters, suckling pig and bacon, and spicy fried chicken.


This basement bar is the perfect place to watch the evening unfold on a weeknight. There is live music, DJs and a cozy fireplace to keep you warm.

Art Bar

Need a good drink on a weeknight? Enjoy a menu filled with botanical-driven menu items and first-rate cocktails at this West Loop bar.

Wicker Park Tavern

This restaurant gives you the chance to listen to live music while enjoying dinner and a drink.

What to See and Do in Chicago

Chicago is a big city, and there are many things to do. So how do you decide how to spend your time? We've put together an itinerary that will help you hit some of the highlights in just 3 days.

Day 1: Downtown Chicago

Aerial View of Chicago Lake Shore Dr at sunrise

Begin your Chicago vacation with a trip down Michigan Avenue. Here are some of the highlights:
The Magnificent Mile. Stretching from the banks of the Chicago River to Oak Street, this stretch of Michigan Avenue is home to luxury hotels, upscale boutiques and world-class restaurants.

Millennium Park. This 24-acre park in the middle of Downtown Chicago features art installations, free music concerts and other popular events throughout the year. Grab some lunch at one of many nearby cafes or food trucks, then take a stroll through Lurie Garden or explore Cloud Gate (aka The Bean).
Navy Pier. Located on Lake Michigan, Navy Pier is home to numerous attractions like rides, museums and more than 50 shops and restaurants. If you're visiting in warmer months, you can also enjoy boat tours of the lakefront and skyline.

Day 2: Visit Museum Campus in Chicago

Shedd Aquarium on Museum Campus, Chicago

The Museum Campus is home to three of Chicago's top museums: Adler Planetarium, Field Museum, and Shedd Aquarium. You can easily spend an entire day here, especially if you have kids with boundless energy who are anxious to see the dinosaurs, mummies, and penguins.

Chicago River Cruise: This cruise is a great way to see the city. You have a choice of a daytime or nighttime cruise and you can choose between a narrated tour or a flat-bottom, open-air boat that provides a 360-degree view.

Day 3: Take in architectural highlights in Chicago

Chicago downtown architecture

You can easily spend a couple of days touring famous Chicago landmarks, but if you're on a tight schedule, be sure to include the Tribune Tower and the Wrigley Building in your itinerary. Both were designed by famed architect Raymond Hood, who also designed the Tribune Tower in Los Angeles.

Day 4: Visit the Art Institute of Chicago

Entrance to the Art Institute of Chicago Museum, Illinois

The Art Institute offers free admission from 4 to 8pm during the summer, so you can marvel at van Gogh's "Sunflowers" and Monet's "Water Lilies" for hours without spending a dime.

Day 5: Visit classic neighborhoods in Chicago

Chicago Old Town Neighborhood

Chicago has 77 neighborhoods, each with its own character and charm. One way to explore them is to take the Chicago Neighborhood Tours bus, which stops at some of the city's most iconic sights and offers an overview of each neighborhood. You get off the bus at a few spots, so you can stretch your legs, take in the sights and snap some photos.

The Magnificent Mile and the Loop are great places to get a sense of Chicago, but they don't really feel like actual neighborhoods. For that, head to Lincoln Park and Old Town on the North Side or Wicker Park or Hyde Park on the South Side.

Lincoln Park and Old Town are convenient to one another, so you can easily visit both in a day: The neighborhood is bounded by Armitage Avenue on the south, Diversey Avenue on the north, Clark Street on the east and Lake Michigan on the west.

The Lincoln Park Zoo is free and opens every day from 10 a.m. to 5 p.m., except for Thanksgiving and Christmas Day; it's not too big for little kids but has enough going on to delight adults as well (and there's a nice cafe if you want to take a break). The zoo also hosts seasonal events including Boo at the Zoo, which takes place in October, and ZooLights in December; both are very popular with families.

Shopping in Chicago

Louis Vuitton store on the Magnificent Mile, Chicago

Chicago has a lot of shopping and with it all located on Michigan Avenue you can easily stay there the whole day and still not see it all. There is a group of stores that make up the Magnificent Mile and it is a good place to start. This is a very long section of Michigan Avenue with a lot of upscale stores. It stretches from the Chicago River to Oak Street and from the North side to the South side.

The Water Tower District

The Water Tower District is located in downtown Chicago. It is near Michigan Avenue which is where all the shopping is located. This area contains mostly converted loft apartments that surround the Water Tower along with other buildings built around it later on. The Water Tower was built in 1869 to replace one that was destroyed by fire. The district also contains restaurants and gift shops as well as an Apple store on Michigan Avenue.

The Magnificent Mile

The Magnificent Mile is located just a few blocks away from The Water Tower. This is where all the big name stores are located. It is near Michigan Avenue between Oak and Rush streets. You can easily walk from here to the Water Tower district. This area also has a lot of restaurants.

Gold Coast

Gold Coast is located just north of The Water Tower. The Gold Coast neighborhood is known for its high-end residential buildings and expensive shops.

Final Thoughts

Cloud Gate Bean with Chicago Skyline

In the end, the best way to spend $10,000 on a trip? Do whatever makes you happy. If it's a lavish trip, go for it. If that means spending some time at home, so be it. But don't let someone tell you that one choice is better than another—only you can do that for yourself. And if you ever have extra money to spend on family or friends, use it to bring joy into their life. Or consider donating it to an organization like Pencils of Promise. You never know how much your generosity can change the world.

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