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Guide to Planning a Family Trip to Chicago

May 23, 2019
14 min read
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Chicago, once known as the “second city,” is second to none when it comes to fun activities, family-friendly cuisine and historic sights. Set at the confluence of the Chicago River and beautiful Lake Michigan, and boasting a range of important architecture, Chicago is also extremely photogenic, even when the weather isn't perfect. I moved west from Chicago when I was a teenager, but every time our family visits, we are delighted to discover more neighborhoods and sights.

The Ohio Street Beach on a warm day. (Photo by Miguel Angel Sanz / Unsplash)
The Ohio Street Beach on a warm day. (Photo by Miguel Angel Sanz/Unsplash)

How to Get to Chicago

Chicago and its environs are served by two international airports: the massive Chicago ’Hare (ORD) north of the city and Midway (MDW). O’Hare is one of the busiest airports in the world and United Airlines’ main hub. ORD is also served by American Airlines, Delta, Spirit, JetBlue, Frontier (remember to take advantage of Kids Fly Free) and Alaska, as well as numerous international carriers. Midway hosts fewer airlines and services, but is your only local option if you want to use your Southwest Rapid Rewards or make use of your Southwest Companion Pass. Midway also hosts flights from Delta.

The two airports in Chicago are pretty far apart, so you may have to balance the importance of award flights and affordability with convenience. Check the distance from the airport to the hotel you choose, and think about how the travel time will impact your schedule. O’Hare offers much more in the way of lounges, dining options and choices and it may be much closer to your final destination. On the other hand, Midway may offer more heavily discounted flights.

Inside the O'Hare International Airport. (Photo by Ben Wicks / Unsplash)
Inside O'Hare International Airport. (Photo by Ben Wicks/Unsplash)

Once you’re on the ground, you have options as far as transportation into the city. The cost of taking the “L” (the Elevated Train, Chicago’s subway) from O’Hare to downtown Chicago is about $5 per person, while from Midway it’s only about $2.50. Meanwhile, an Uber or Lyft can cost $25 (Midway) or $30 (O’Hare), or more during busy periods. Unless you have too much luggage (or too many tired travelers) and need the convenience of door-to-door transport, you’ll save money and potentially time using public transportation. The Chicago Transit Authority provides an online trip planner that you can use to figure out your transportation from either airport, as well as how to get around once you’re in the city.

Boarding the L Train to O'Hare (Summer Hull / The Points Guy)

A car in the city may be more trouble than it’s worth, but there are plenty of major car rental agencies within both airports if you choose to go that route.

Related: The 7 Best Starter Travel Credit Cards

Family-Friendly Neighborhoods

Many of Chicago’s most convenient neighborhoods for hotel stays or condo rentals are along the streets a few blocks west of Lake Michigan, on or near the stretch known as the Magnificent Mile. In this area, you’ll find loads of shops, eateries and attractions all within walking distance of each other. Michigan Avenue is known for its upscale shopping and impressive architecture, and that’s where you’ll find Chicago’s famous Water Tower, one of the few structures to survive the Great Chicago Fire of 1871. Built in 1869, the lovely Gothic-revival Water Tower now stands as a memorial to the city’s recovery. The Magnificent Mile is also close to Navy Pier, home to the Centennial Wheel (adult tickets are $18, kids 3–11 cost $15 and children under 3 are free) and Chicago Children’s Museum (admission is $14.95 for adults and kids; those under 1 are free). The pier is also a departure point for a variety of lake cruises and tours.

A view at dusk of the Centennial Wheel on Navy Pier. (Photo by Gautam Krishnan / Unsplash)
A view at dusk of the Centennial Wheel on Navy Pier. (Photo by Gautam Krishnan/Unsplash)

If you’d rather settle into an area with more of a residential neighborhood feel, consider the quieter Lakeview/Lincoln Park area. You’ll be farther from some name attractions but closer to the lake and the free Lincoln Park Zoo and surrounding park. With its handsome brownstones and lovely water views, this neighborhood is pleasant and stately.

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A polar bear at the Lincoln Park Zoo! (Photo by Matthew Mazzei / Unsplash)
A polar bear at the Lincoln Park Zoo. (Photo by Matthew Mazzei/Unsplash)

Sports fans might enjoy a hotel or Airbnb in the more lively neighborhood of Wrigleyville, where pretty residential streets radiate out from the Chicago Cubs’ historic ballpark. There are plenty of souvenir shops, eateries (and drinkeries) in this neighborhood to serve the baseball-loving crowd, but this is also a friendly, charming neighborhood that can serve as a unique home base.

Best Points Hotels in Chicago for Families

Here's a look at some of the points hotels TPG feels are a good bet for families in Chicago.

Intercontinental Chicago Magnificent Mile

The indoor pool at the Intercontinental Chicago Magnificant Mile. (Photo courtesy of Intercontinental Chicago)
The indoor pool at the Intercontinental Chicago Magnificent Mile. (Photo courtesy of Intercontinental Chicago)

This centrally located hotel offers rooms with two double beds from 50,000 IHG Rewards Club points per night. Rooms available on points (classic two-bed rooms) are not as spacious as some, but many come with cool city views. All include bottled water, a coffee maker, premium TV channels and use of the hotel’s indoor pool.

IHG Rewards Premier Credit Card holders get the fourth night free on award stays, which brings the per night cost down to 37,500 points per night.

For points plus cash (45,000 + $33), families can book the same classic two-bed room plus the InterContinental’s Summer Scavenger Hunt package. Your kids will receive a Chicago Scratch-off Scavenger Hunt with 30 destinations to get everyone excited about seeing the Windy City. The package also includes breakfast for up to two kids, milk and cookies, an adventure backpack, a Lincoln the Lion plush toy, coloring book and travel journal.

Embassy Suites Chicago-Downtown

Inside the Embassy Suites Chicago Downtown. (Photo courtesy of Embassy Suites)
Inside the Embassy Suites Chicago Downtown. (Photo courtesy of Embassy Suites)

Five blocks from Navy Pier, Embassy Suites offers standard two-double bed two-room suites for 39k–60k Hilton Honors points/night. Included in the rate are a hot made-to-order breakfast for everyone, and the hotel’s evening happy hour with complimentary drinks and snacks.

Hilton has a number of cobranded credits cards that will help you earn Hilton Honors points on everyday spending. Find out which Hilton credit card is best for your family.

SpringHill Suites Chicago Downtown/River North

A guest room at the SpringHill Suites Chicago Downtown. (Photo courtesy of SpringHill Suites)
A guest room at the SpringHill Suites Chicago Downtown. (Photo courtesy of SpringHill Suites)

In the River North neighborhood, between the Magnificent Mile and Millennium Park, SpringHill Suites offers rooms with two-double beds plus a sofa bed from 35,000 Marriott points/night (or use an up to 35k free night certificate like the one you get on your card anniversary with the Marriott Bonvoy Boundless Credit Card). Amenities such as complimentary breakfast and Wi-Fi, and a top-floor indoor pool-with-a-view will make your family’s stay comfortable and memorable, in that order.

Hyatt Place Chicago/Downtown-The Loop

Though it’s situated in a business district, this Hyatt is less than a mile from attractions such as the Art Institute of Chicago, the Skydeck at Willis Tower and the Chicago River Walk. This hotel offers excellent amenities for families: two-queen bed rooms, including a sofa bed (or a king room with a sofa bed), can be had for 15,000 World of Hyatt points/night. The rooms are modern, comfortable and spacious. There’s also a 24-hour fitness center, an indoor pool and free Wi-Fi all over the hotel. Plus, breakfast is free for the whole family as long as you book the room through Hyatt. Since this hotel is just a Category 4, you can even use a Category 1 - 4 award certificate.

You can transfer Chase Ultimate Rewards to your Hyatt account on a 1:1 basis or earn more points with the World of Hyatt Credit Card that currently offers a welcome bonus of earn 30,000 bonus points after spending $3,000 on purchases within the first three months from account opening. Plus, up to 30,000 more bonus points by earning 2x bonus points total on purchases that normally earn 1x bonus point, on up to $15,000 in the first six months of account opening.

Best Western Plus Hawthorne Terrace Hotel

The Best Western Plus Hawthorne Terrace Hotel. (Photo courtesy of Best Western)
The Best Western Plus Hawthorne Terrace Hotel. (Photo courtesy of Best Western)

Just north of Lincoln Park, in the Lakeview district, is this attractive Best Western offering two-double bed rooms for 36,000 points per night. This is a peaceful spot, yet it’s close enough to enjoy all that the vibrant city offers.

Families who stay here can enjoy jogging, playing or renting bikes on the lakefront, and each room comes with a complimentary full breakfast and a morning paper. The hotel is walking distance to Wrigley Field as well as a variety of neighborhood restaurants.

Wyndham Grand Chicago Riverfront

If you have some Wyndham Rewards points burning a hole in your pocket, you can spend 30,000 of them per night at the Wyndham Grand Chicago Riverfront. This hotel is easy walking distance to shows, restaurants and of course, the river. Tip: Ask for a river-facing view for a real treat.

View from the Wyndham Chicago Riverfront (Summer Hull / The Points Guy)

Planning Tips

Chicago is a beautiful city in any season, and those of us who grew up in the area have special memories of snow-laced tree branches and the frozen lakeshore. However, choosing a milder time of year makes it easier to cover more ground with a family. If you can carve out the time for a family vacation during late spring, when trees are leafing out and the city has thawed, that’s a wonderful time to visit. The colorful foliage and crisp temperatures in autumn are also nice. In summer, your family can enjoy the lakeside beaches and the ballpark, though the heat and humidity can be intense.

A frozen-over Chicago River. (Photo by Yomex Owo / Unsplash)
A frozen-over Chicago River. (Photo by Yomex Owo/Unsplash)

City of Festivals

If the sun is out, Chicago is probably holding a festival somewhere. Some of the biggest are the annual Blues Festival (June), the food-and-music extravaganza Taste of Chicago (July) and the four-day Lollapalooza rock event (August). The free Grant Park Music Festival (June) has been a favorite among classical music-loving families for more than 80 years. Before you firm up your travel dates, search the listings in Chicago’s weekly news and arts paper, the Reader, for fun events to target.

A crowd watching the Grant Park Symphony at the Jay Pritzker Pavilion in Chicago. (Photo by Education Images/UIG via Getty Images)
A crowd watching the Grant Park Symphony at the Jay Pritzker Pavilion in Chicago. (Photo by Education Images/UIG via Getty Images)

Sports Schedules

Please the sports fans in your family by planning a trip that dovetails with a ballgame or two. Chicago is home to two historic baseball parks: the Cubs’ Wrigley Field on the north side and the White Sox’s Guaranteed Rate Field to the south. The Bears’ massive neo-classical amphitheater, Soldier Field, welcomes football fans. The arena that Michael Jordan built — the Bulls’ United Center — is an exciting destination for basketball lovers.

Wrigley Field, home of the Chicago Cubs. (Photo by Blake Guidry / Unsplash)
Wrigley Field, home of the Chicago Cubs. (Photo by Blake Guidry/Unsplash)

Bottom Line

The City of Chicago offers a deep well of history, culture and beauty, as well as lots of places to play. Has your family visited the Windy City? What were your favorite sights to see?

(Summer Hull / The Points Guy)

Keep planning your Chicago trip:

Featured image by (Photo by Josh Howard / Unsplash)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.