Top 20 Chicago Staycation Ideas for Family and Couples

I personally find the city of Chicago to be very accommodating. Whether you’re looking for something to do with your family or a romantic staycation, you can choose from plenty of options.Chicago Staycation Ideas for Family

Like any other modern city, life in Chicago can be pretty hectic. You will require a break if you have been in the town long enough. That is where Chicago can comfort you. You can choose from numerous staycation options the city has to offer.

I decided to compile Chicago staycation ideas for families and couples when I was looking for one. That is what I will share today.

What Is a Staycation?

A staycation is a vacation near or in your city. It eliminates or minimizes the travel part from the holiday.

Types of Staycation

Not every staycation is equal. When you look at the types, there are quite a few of them. The first three depend on who is coming with you on the staycation, and the rest depend on the accommodation you choose.1. Family

Family staycation involves your entire family rather than just the adults or a couple.

2. Romantic

Sometimes, you and your partner need to de-stress yourself. That is when it makes sense to go on a romantic staycation with your partner.

3. Solo

Do not be surprised if you need a break and head out solo to stay at a hotel or resort in your city. Solo staycations are becoming more and more common these days.

4. Hostel

A staycation does not just involve a hotel or resort. These days, hostels are offering affordable staycations.

5. Glamping

Glamping stands for glamorous camping. If you’re planning to head over to such a camp in and around Chicago, you can experience the glamping staycation firsthand.

6. Hotel

This is the most common type of staycation. Choose a five-star hotel in your city and enjoy what it has on offer.

7. Caravanning

Use your camper or rent one and head over to a camper lot. That is certain to provide you with a break without traveling a lot.

8. Private Accommodation

The list in this article consists of many private accommodations and homes you can rent for a shorter duration to explore and stay in a new part of your city. That is what private accommodation staycation involves.

How to Prep for Your Staycation?

Without proper prep, your staycation can turn into a stressful experience. Fortunately, there are some things you need to take care of.

1. Finish Chores in Advance

Instead of keeping everything for the last day, finishing your chores in advance is a good idea. Whether you want to send a few emails or let your office know that you won’t be coming for a few days, you must finish all such chores in advance.

2. Plan the Meals

Not necessarily; every staycation option will provide you with all the meals. You shouldn’t leave the meal arrangements to the last minute. If you plan on visiting the restaurants nearby, prepare a list in advance.

In case you want to patronize the restaurants in the hotel itself, check out the restaurants and their offerings in advance. That way, there will be no last-minute stress when looking for food.

3. Familiarize Yourself with the Place

Of course, you will be heading to a different suburb or a neighborhood of your city while on staycation. If you familiarize yourself with that neighborhood, it will become easier to explore the surroundings and the tourist attractions.

4. Explore the Vicinity

Do not just stay in your home. Every neighborhood has something to offer. Explore the vicinity whenever you can. Once you have a list of the attractions nearby in advance, it becomes easier to enjoy your staycation.

5. No Last-minute Packing

Last-minute packing can add to the stress of your staycation. Make sure that your bags are packed the night before.

Benefits of a Staycation

Once you consider these benefits, it is easy to understand why it makes sense to embark on a staycation from time to time.


A staycation will save you a lot of money compared to traveling far and wide. That is why; you can indulge in frequent staycations.

Easy to Se-stress

Since little to no traveling is involved, it is not a stressful experience. You can quickly reduce your stress and rejuvenate yourself.

You Get to Explore New Neighborhoods

Nobody has explored their city entirely. That is why, when you go on a staycation, you can explore an entirely new neighborhood.

Achieve Proper Work-Life Balance

It’s difficult to take a holiday for a week or so. However, staycation allows you to take a two-day holiday in and around your city. Doing so will help you achieve a proper work-life balance.

Our Top 20 Chicago Staycation Ideas for Couple and Family

A. Resorts and Hotels

1. The Gwen

The Gwen

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The Gwen has all the modern amenities which a hotel can offer. Apart from that, the room sizes are comparatively larger at 375 ft.² to 425 ft.². If you’re in a mood to splurge, it offers suites up to 3000 ft.² as well.

Services like complimentary bicycles, Wi-Fi, laundry, 24-hour fitness center ensure that you won’t have to step out of the hotel for anything.

Combine all that with the 1930s style, central location, and it is easy to understand why it is perfect for a staycation.

2. Grand Traverse Resort

Grand Traverse Resort

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Don’t mind a drive? If so, Grand Traverse Resort is a good choice for you. Located five hours away from Chicago, it is not that far either.

The USP is 1400 acres of land on which it is based. That is not any land but rather the Lake Michigan shore. The location and the well spread out area have made it famous among families.

With four 18-hole golf courses along with a golf school, you can have a gala time at the resort.

The spa itself is spread across 100,000 ft.². That’s not all! You get to choose between a tennis center, sauna, indoor swimming pools, whirlpools, and a relaxation room. You will have numerous options when you head over to this resort.

The options do not just end at the amenities. You can choose between the 17-story tower, rooms in the hotel, and condominiums for your accommodation. Numerous indoor restaurants serve you delicacies that you couldn’t even imagine.

What more do you need in a staycation? Hence, it is one of my favorite staycation place when in Chicago. It also very nearly from Acadia.

3. The Abbey Resort

The Abbey Resort

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In case you want something close, the Abbey restaurant is located just a 100-minutes drive away from Chicago. There is no shortage of options with 90 acres and 334 rooms, along with numerous villas and suites.

It has plenty of amenities to offer like:

  • 35,000 ft.² spa
  • Aerobics studio
  • Indoor and outdoor swimming pools
  • Golf course
  • Arcade
  • Multiple restaurants

Whether looking for a romantic staycation or one where you can take your family, this qualifies in both categories because of the numerous accommodation options and a widespread area.

4. Swissotel Chicago

Swissotel Chicago

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How about a hotel located right on the Chicago River?

Swissotel Chicago offers a centralized location, a short walk away from the magnificent river. The reason why I like this hotel is that it provides a kids’ suite. Once you book the same, your kids will be able to explore several items in the room like games, books, bathrobes, thematic decoration, and so on.

If you’re especially taking a staycation for your kids, there is no better option than this one.

5. The Edgewater

The Edgewater

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Many times, a staycation can involve getting away from the city. You can head over to Madison, Wisconsin, which is like a three-hour drive away. While the city is home to numerous hotels, you need to look out for the Edgewater Hotel.

Since it had reopened in 2014, it has garnered raving reviews due to the ice skating rink, among other amenities like the spa. Family skate night, as well as Icehouse Friday night, can help you bond with your family while visiting this hotel for a staycation.

6. The Newport Resort

The Newport Resort

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Do not be surprised if this list consists of numerous resorts in and around Chicago. That is because resorts are perfect for a staycation.

Another great option is the Newport resort, approximately a 4-hour drive away from Chicago. This beachside property offers you 59 rooms along with suites.

It goes a step further from the usual resorts by offering you:

  • Game room
  • Swimming pool
  • Fitness center
  • Library
  • Lobby Lounge
  • Garden and so on

The reason why it is famous among families is because of the beach nearby.

7. The Knickerbocker on the Lake

The Knickerbocker on the Lake

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You can have a comfortable staycation at the Knickerbocker in Milwaukee, with walking distance to theaters, restaurants, and museums. Choose among 160 different rooms to find the one which suits your requirements perfectly.

With rejuvenating spa services on offer and a 24-hour fitness center, you can have a relaxing staycation with your family. Since it is just a 90-minute drive away from Chicago, it will not take much of your time either.

8. Sevenoaks


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I understand that some of you might be scouting this list for a completely private and romantic staycation idea.

Here it is!

Sevenoaks is an adult-only cottage property. It consists of only 11 cottage properties that are spread across the area.

Features like lounge chairs, a fire pit, and a water feature give a calming ambiance to the whole place. Whether you want to play golf, indulge in a spa, or go for a hike, you can do all of that and more.

In terms of intimacy and privacy, it is undoubtedly a good option located just ninety minutes away from Chicago.

9. Washington House Inn


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Spending a lot of money is not always necessary to enjoy a staycation around Chicago. Washington House Inn is a short two-hour drive away from Chicago in Cedarburg and is the perfect option for a budget staycation.

Amenities like complimentary afternoon wine, elegant accommodation options, free high-speed Internet, and cheese social hour make it unique from the other staycation ideas on this list.

The town of Cedarburg has over 70 boutique shops, museums, and much more to explore. With all-inclusive packages available, you need not worry about any surprise charges. The unique nature of the accommodation and the location in a quiet little town make it worth exploring.

10. Peninsula Chicago

Peninsula Chicago

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For many, indulging in an extended and rejuvenating spa session is the idea of a staycation. If you too are one of them, go with the best spa hotel in Chicago.

Yes, it’s the Peninsula. Not only, it has the best spa in Chicago, but one of the best 5-star hotels. If you like to be pampered, choose from their luxury accommodation options and head over to the 19th floor of this 20-floor hotel. There you can enjoy rejuvenating spa therapies along with exploring the skyline of the city.

There is no need to head anywhere else to satisfy your hunger with critically acclaimed restaurants in-house. In other words, if you’re looking for a luxurious staycation, it doesn’t get any better than this.

11. Ritz Carlton Chicago

Ritz Carlton Chicago

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Another luxurious hotel on our list is Ritz. The Ritz-Carlton Chicago is located pretty close to Lake Michigan. There is no shortage of options with numerous suites and rooms to choose from.

You can also try out their culinary delights along with the spa, as they have three different in-house restaurant options. The pool and fitness center can keep you relaxed and calm.

Very few hotels in Chicago can pamper you in the lap of luxury. This hotel is one of them.

12. Kimpton Hotel

Kimpton Hotel

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Nothing is better than a boutique hotel for a stylish staycation. The Kimpton Hotel can fulfill this requirement. It has everything you can ask for on a staycation. For example, the pool on the 17th floor can provide you with gorgeous views of the city.

If you want to explore the local flavors, they have the Sable Kitchen & Bar. Along with the wellness program and a well-equipped gym, you can have a relaxing time at the hotel.

If you want to explore the city, they offer PUBLIC bikes. Daily wine hour at night can further help you unwind on your staycation. Not only that, the pet-friendly rooms can ensure that you can enjoy a staycation with your pets.

In terms of amenities and offerings, Kimpton is second to none.

13. Four Seasons Chicago

Four Seasons Chicago

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Four Seasons, the name itself, is a mark of luxury. Apart from the comfort, it also offers an unrivaled view of the skyline and the lake. The hotel also houses the restaurant of Chef Jonathon Sawyer. That is why; tasting unique American delicacies will keep you occupied throughout your staycation.

Numerous spa services, along with other amenities like a fitness center, can fulfill all your requirements when you head over to 4 seasons for a staycation with your family.

14. Park Hyatt Chicago

Park Hyatt Chicago

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Want a hotel close to the magnificent mall?

If so, it doesn’t get any better than Park Hyatt Chicago. The kids camp inside the hotel makes it one of the best staycation ideas for families. That doesn’t mean adults won’t have a good time. Nomi Spa in the Hotel ensures that you will be fully rejuvenated when you checkout.

With the location, luxury, amenities, and excellent spa treatments on offer, it is one of the best staycation hotels to choose.

15. The Mansion Bed and Breakfast

The Mansion Bed and Breakfast

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The Run of the mill owners might not suit everybody. That is why something like The Mansion Bed and Breakfast is a good idea to spend your staycation at. This place can serve you well in this regard. Since it is just 35 miles away from Chicago, reaching it isn’t an issue.

On the estate, you will find private houses that were built in 1907. However, the Mansion is full of modern amenities like:

  • Cable TV
  • Wireless Internet
  • Premium mattresses and pillows
  • Hair Dryer
  • Desk
  • Ironing board and iron and so on

Depending on the room which you choose, you can easily enjoy private baths, terraces, an Electric fireplace, or a whirlpool tub in your room. All this, coupled with the 1907 estate, makes it one of the most romantic staycation ideas in and around Chicago.

16. Galena Log Cabin

Galena Log Cabin

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Enjoying a staycation in the lap of nature is certainly possible when you’re in Chicago. The Galena log cabin is the perfect option for the same. The entire property is spread over 45 acres. Depending on the cabin you choose, you can get a single room cabin or one over 650 ft². The choice is yours.

Despite being a cabin, you get to enjoy satellite TV, double beds, microwave, gas fireplaces, refrigerators, Central air conditioning and heating, and so on.

However, you will have to embark on a 2.5-hour drive to reach the place. But, when you look at the farm on the property, you will realize that it is well worth it.

B. Private Homes and Gateways

17. Logan Square Apartment

Logan Square Apartment

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For a more intimate and homely feel, you can run into this two-bedroom apartment in Logan Square. The bright interiors coupled with a fully functional kitchen and a bike rental station at walking distance ensure that you can easily enjoy your time in Chicago.

18. Industrial Stylish Loft

Industrial Stylish Loft

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It is a perfect choice if you’re on a small budget. The Loft has single bedrooms, but the industrial interior makes it worthwhile. The king-sized bed coupled with free Netflix ensures that you can enjoy your time in this stylish Loft. It is a twenty-minute drive from the airport and is pretty well connected.

If you do not have a high budget for a staycation, this one can serve you well.

19. Bella Villa

Bella Villa

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The name of this property is a bit confusing. It is not a villa but a second-floor apartment. Since it is pretty close to the University of Illinois and the Illinois medical center, it is always in demand. Despite that, the three bedrooms ensure one of the best stays with your family.

With a fully furnished apartment, along with modern interiors, it is an excellent spot for a staycation with your family.

20. Chicago Resort Home

Chicago Resort Home

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There are very few accommodation options that combine the amenities of a resort and the privacy of a home. This three-bedroom home does. It is located in safe surroundings and features eight beds. It is spread across 1200 ft.², providing plenty of space for your family.

The McKinley Park neighborhood in which it is located is well connected with the entire city. That makes it a great budget option.

Frequently Asked Questions

How much does the Chicago staycation cost?

Depending on your option, it can cost you $50 per night for a room to $500 for a suite.

Is a staycation in Chicago worth it?

Yes, a staycation in and around Chicago is worth it as it provides you with a break from the busy city life.


Banish any stress you might have by opting for any of these staycation ideas when you’re in and around Chicago.

With the list comprising Chicago staycation ideas for family and couples, there is no reason you shouldn’t find a suitable one. I have experienced quite a few of these hotels/resorts/homes and had a great time.

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