Answer: Chicago's Blue Line is a great option for getting into the city and traveling to Rosemont, especially if you're traveling with a toddler. Many hotels near the Blue Line provide easy access to public transit and are also close to parks, museums, and family-friendly amenities. Here are a few options for hotels that are conveniently located near the Blue Line and also cater to families with young children:

Answer: With a 5-hour connection at O’Hare International Airport (ORD), you have a good amount of time to relax, explore the terminals, and even stretch your legs. Since your international flight is departing from a secure area, your options without leaving security are somewhat limited to what is accessible past the checkpoints, but there are plenty of ways to make the time enjoyable.

Answer: For a short 2-night stay in Chicago, particularly when staying in the Magnificent Mile area, deciding on CTA payment options depends on how much you anticipate using public transportation beyond your airport transfers. Since you plan to walk a lot but may occasionally use trains or buses, here are some considerations.

Answer: You’re right: there really aren’t many great “grab-and-go” food / snack spots along the southern stretch of the Chicago Lakefront Trail (LFT), especially between the Museum Campus and Promontory Point. That section is more residential and park-land than commercial, so don’t expect the density of food trucks or quick-service stands you might find farther north.

Answer: Traveling from Chicago’s airports to the Drake Hotel via public transit is possible, but there are differences depending on whether your party is coming from O’Hare or Midway, and some practical considerations to keep in mind.

Answer: Arriving at O’Hare at 8pm on a Monday, you have a couple of convenient options to get to River North: taxi or rideshare (Uber/Lyft). Both are safe and commonly used by visitors, but there are differences in price, convenience, and wait time.

Answer: If you're looking for animal-oriented experiences in the Chicago area or nearby southern Wisconsin, there are several places that focus on rescue, rehabilitation, and animal sanctuaries rather than traditional zoos. Here are some excellent options for a unique and meaningful experience:

Answer: Traveling from O’Hare International Airport (ORD) to the InterContinental Hotel on Michigan Avenue is fairly straightforward. Since you are arriving around lunchtime on a Thursday and traveling with two people over sixty, comfort and convenience should be prioritized over the cheapest option.

Answer: For a family visit to Chicago in early to mid-August, focusing on neighborhoods that are safe, family-friendly, and close to cultural attractions is key. Chicago has a number of areas that combine convenience, green space, and access to museums, making them ideal for families traveling with teens.

Answer: It sounds like you're looking for a fun, relaxed spot to enjoy some great food and a comfortable setting for conversation, without breaking the bank or dealing with a cover charge for live music. Chicago has plenty of options for a Saturday night with good eats and a laid-back vibe. Here's a breakdown of the places you mentioned, along with a few additional recommendations:

Answer: Both Virgin Hotel and Stay Pineapple are excellent options for your anniversary trip to Chicago, and each has its own unique appeal. Here’s a breakdown of both to help you decide which one might suit your needs best:

Answer: Wicker Park is generally considered a safe neighborhood, but like any urban area, it's important to stay aware of your surroundings, especially when out at night as a solo traveler.

Answer: To get from O'Hare to downtown Chicago using the CTA (Chicago Transit Authority) trains, you have a couple of options for payment, and you can indeed use your credit or debit card directly, much like you would in London.

Answer: For your weekend plans, it makes sense to prioritize location based on convenience for both the Northwestern University (NWU) football game in Evanston and the Taste of Chicago in Grant Park. Given your preference for minimal walking due to knee issues, staying in downtown Chicago is likely the best compromise. You can use public transportation to reach Evanston for the game without a long drive, and you’ll be right at the center for the Taste of Chicago.

Answer: Little Italy and University Village are both great neighborhoods in Chicago, and you're in for a treat during your stay. Here's some detailed information about the area and what to expect:

Answer: If you’re looking for some evening activities on Sunday, November 24th in Chicago near Millennium Park, here are a few ideas that might work for you, especially considering that the Art Institute closes at 5:00 PM:

Answer: Hi there! It sounds like you're planning an exciting trip to Chicago with your family! Below are some thoughts on the hotels you're considering, as well as some general recommendations to help you choose the best fit for your needs.

Answer: It sounds like you had a wonderfully packed and enjoyable weekend in Chicago, managing to balance sightseeing, food, and local experiences in just a short visit. Here’s a breakdown and some insights based on your trip report:

Answer: It sounds like you're going to have a wonderful time in Chicago during the holiday season! There's so much to see and do, especially with the Christmas decorations and lights. I'll try to break down your questions and provide some useful suggestions:

Answer: March can be a bit of a mixed bag when it comes to visiting Chicago, especially if you're not used to the colder winter weather. It’s true that the weather in Chicago during this time is unpredictable. You might experience a mix of chilly temperatures, occasional snowstorms, and even a few days that feel like early spring. However, this doesn't necessarily make March a bad time to visit – it just requires a little more preparation. Here’s what you can expect and some tips for making the most of your trip:

Answer: Visiting Chicago with your family can be a lot of fun, especially with kids in tow. Here’s a detailed breakdown for your upcoming trip questions:

Answer: It sounds like you're planning a great trip to Chicago! Both the Congress Plaza Hotel and River Hotel are located in central Chicago and are relatively close to major attractions such as museums, restaurants, and music venues. Here's a detailed breakdown of each hotel, as well as some other recommendations to help you make an informed decision:

Answer: Chicago is known for its incredible architecture, and taking a river tour is one of the best ways to explore and learn about the city's iconic buildings while enjoying the beautiful views. Since you're looking for an informative, entertaining, and comfortable tour (and cold weather doesn't bother you), here are some of the top architecture boat tours in Chicago that I recommend:

Answer: It's great that you're planning a trip to Chicago! For the activities you mentioned, here’s some advice on when to book them in advance:

Answer: It sounds like you're trying to balance budget-friendly accommodations with your desire to see the best of Chicago, which is completely understandable, especially if you're traveling with kids. While staying near Midway Airport might save you some money on lodging and parking, it’s important to weigh the pros and cons, especially given the locations you plan to visit in the city, such as Millennium Park, the Skydeck, and an architecture tour. Let’s break down the decision to see if it’s the right fit for you:

Answer: Deciding between visiting Chicago at Christmas or New Year’s depends on what kind of experience you’re looking for, as both have their own unique charm, activities, and considerations.

Answer: Hi there! It sounds like you have a fun Chicago trip planned, and the Navy Pier fireworks will be a great way to start things off with the kids. Here's some advice on how to make the most of the experience:

Answer: The Taste of River North is a fantastic event for anyone visiting the area during that weekend! It’s an annual food and drink festival showcasing some of the best restaurants and bars in the River North neighborhood. The event typically features local chefs offering tasting portions of their dishes, along with craft cocktails, beer, and wine. It’s a great way to experience the local culinary scene in one place, with many options to try. It also tends to have a lively atmosphere, making it perfect for a fun night out.

Answer: The intersection of Wacker Drive and Michigan Avenue puts you right in the heart of Chicago’s Loop, just a short walk from the Chicago River and many dining options that cater to both locals and visitors. Since you’re finishing a late-afternoon architecture boat tour, it’s convenient to choose somewhere within a 5–10 minute walk along the river or nearby streets. Here are some excellent options:

Answer: In Chicago, the vast majority of restaurants, bars, and shops accept credit and debit cards. However, it is true that you may encounter a few “cash only” establishments or places that add a small surcharge for card payments. This is more common in smaller, independently owned bars, cafes, and casual restaurants rather than large chains.

Answer: Yes, both Millennium Park (where the Bean is located) and the Field Museum in Chicago are very Uber-friendly, as these are high-traffic tourist areas with plenty of pick-up and drop-off points. Using Uber to travel between the two locations is straightforward and convenient, especially if you want to avoid dealing with parking in downtown Chicago.

Answer: The South Loop area is a great place to stay for tourists visiting Chicago! It’s conveniently located near many of the city's top attractions and offers a blend of urban charm, historical sites, and modern amenities.

Answer: Happy early anniversary! Chicago has some wonderful spa options that will make for a perfect relaxing experience, and since you're staying at The Langham, you're already in a prime location to explore some top-tier places nearby. The Langham’s spa is great, but if you're looking to check out other options in the area, here are some highly recommended spas that offer couples massages and facials, perfect for your anniversary getaway:

Answer: Both the Swissotel and the Westin are great hotel options in Chicago, but they each offer a different vibe and experience. Below are the key points about both hotels to help you decide which one fits your needs for the trip to watch the Astros play the White Sox.

Answer: Visiting Chicago during the 4th of July weekend is a great experience, but it does come with some challenges due to the crowds and events, particularly with the NASCAR race and the holiday festivities. Here are some tips to help you make the most of your trip.

Answer: Both the Willis Tower (formerly known as the Sears Tower) and 360 Chicago offer incredible views of Chicago, but each has its unique features that might make one a better choice for your visit, especially if you're considering sunset views.

Answer: It sounds like you had an amazing trip to Chicago, and thanks for sharing your detailed experience! It’s great to hear how well everything went, from the art museum to the food and the unique spots you visited. Here are some helpful details based on your trip that others might find useful:

Answer: To visit the famous "Home Alone" house from the movie, which is located in Winnetka, a suburb north of Chicago, you'll need to plan your transportation from downtown Chicago. Here are a few options for how you can get there via public transportation:

Answer: It sounds like you’re in for a fantastic trip to Chicago! April is a great time to visit, with spring in full bloom and plenty of things to do. Below, I’ll break down some recommendations for each of your interests to help make the most of your 9-day trip.

Answer: Pre-booking a taxi from O’Hare International Airport to downtown Chicago is a smart idea, especially if you want a guaranteed ride, avoid the crowds at the taxi lines, and have a smooth arrival after a flight. Chicago has several reputable taxi services that allow pre-booking, and while Uber and Lyft are popular alternatives, traditional taxis can offer a more predictable fixed fare if requested in advance.

Answer: To travel from Terminal 5 (T5) to Terminal 2 (T2) at O'Hare for your hotel shuttle, you have a few options, but it’s important to plan your route since you’ll be handling plenty of luggage.

Answer: It can be a bit tricky to find hotels in Chicago that allow 18-year-olds to check in, as many places do have a minimum age requirement of 21 or even 25. However, there are still some budget-friendly options in safe areas where you can book a stay as a young traveler. Here are a few suggestions:

Answer: Traveling from O’Hare Airport to Kenosha by train is definitely doable, but it requires a transfer in downtown Chicago from the CTA to Metra commuter rail. Here’s a detailed breakdown of how to make the trip and what to expect.

Answer: Jet and Fly shuttles operate at O'Hare International Airport, and they provide convenient transportation to and from the airport. For their drop-off and pick-up locations:

Answer: The situation with Row A at the Cadillac Palace Theater is fairly common for popular shows like Phantom, Lion King, and other big productions. Here’s a detailed breakdown:

Answer: The Grant Park pickleball courts in Chicago are part of the city's growing effort to provide outdoor recreational sports options. They are generally well-maintained and attract players of all skill levels, from beginners to more advanced players. Since pickleball has been increasing in popularity nationwide, the courts can get moderately busy, particularly on weekends and during early evening hours.

Answer: It sounds like you're in for a truly luxurious and relaxing solo trip to Chicago! Since you're aiming for a relaxing "me" trip with some splurge-worthy experiences, here are some tailored recommendations for spas, dining, and other relaxing activities that could make your stay even more enjoyable.

Answer: Chicago is a great city for anyone interested in organized crime history, especially from the Prohibition era. While many people opt for organized tours to explore these sites, there are still plenty of fascinating places you can visit on your own to get a taste of the city's colorful mob past. Here are a few spots and ideas for exploring Chicago’s mob and Prohibition history independently:

Answer: Chicago is a wonderful city with plenty of family-friendly attractions, even for a 2-year-old! If you're looking to make the most of your day with a little one, here's a list of fun activities that can keep both you and your toddler entertained:

Answer: Hi there!

Answer: If you're planning to head to O'Hare Airport via taxi or ride share between now and March 17th, be aware that there will be some construction-related disruptions on the outbound Kennedy Expressway (I-90). The work is expected to impact travel times, especially as the outbound local lanes will be closed, and only the Edens Expressway access lanes will remain open for express traffic.

Answer: It's great that you're returning to Chicago and looking to experience the River North area! Each of the hotels you are considering has its own set of advantages, so let’s break down each option to help you make the best choice for your family.

Answer: It sounds like you're in for an exciting day at Soldier Field! Given the timing of the game and the places you're visiting afterward, it’s good to plan your transportation carefully to avoid stress, especially with the crowds post-game. Here's some advice:

Answer: It sounds like you have an exciting layover planned in Chicago on St. Patrick's Day! The St. Patrick's Day festivities are sure to make the downtown area (especially near Union Station) crowded, so it's a great idea to consider exploring other neighborhoods for a more relaxed experience while still being close to some great bars and restaurants.

Answer: Choosing the right neighborhood for your stay in Chicago really depends on the kind of experience you're looking for. Here's a breakdown of the three neighborhoods you're considering: The Loop, River North, and Magnificent Mile. All three are within walking distance of key attractions, but each offers a slightly different vibe.

Answer: Hello Lois,

Answer: To get to the Brown Line from Jackson Station on the Blue Line, and then onto the Pink Line for your architecture tour, follow these steps:

Answer: Hi there! What a wonderful idea to bring your granddaughter on a birthday trip to Chicago! Chicago offers a wide range of activities for children who love science, space, and museums, so she’s sure to have a memorable time. Since your trip is in January, you’ll want to plan for some indoor activities, but don’t worry — Chicago has plenty of options to keep both of you entertained, even when it’s chilly outside.

Answer: Congratulations on your upcoming wedding! For your wedding night in downtown Chicago, you’re looking for a romantic, relaxing experience, so I’ll go through the options and provide my thoughts on each hotel to help you decide. Based on your preferences for a soaking tub, a rooftop bar, good food, and a potential jazz club, here’s a breakdown of the three hotels you mentioned:

Answer: If you're looking for a hotel in Chicago that's conveniently located near a Blue Line station to O'Hare, you have several good options, particularly along the western and near-northwest neighborhoods. The Blue Line is the most direct train route to O'Hare, so staying near it will make your airport trips very easy. Here are a few options for hotels that are located near Blue Line stations:

Answer: A 12-hour layover at O'Hare International Airport (ORD) can certainly feel long, but luckily, there are several lounge options that can help make your time there more comfortable. Since you're flying business class on British Airways and holding MVP Gold status with Alaska Airlines, you're eligible for lounge access. Here’s what you can expect:

Answer: The Skydeck at the Willis Tower (still lovingly called the Sears Tower by many locals!) does use timed-entry tickets, and those do help manage the flow. However, during peak visitor periods—summer, holidays, long weekends, and school breaks—you can still expect some waiting even with a reserved time.

Answer: If you’re looking to experience the most festive Christmas décor in Chicago’s Loop area, several hotels go all out with their holiday decorations. Here are some of the most decorated hotels that make a real spectacle of the season:

Answer: Chicago is a fantastic city to visit, and staying in a self-catering apartment can offer you the flexibility and comfort you might prefer. Here are some great neighborhoods in Chicago where you can find one-bedroom apartments with easy access to public transport and close to attractions:

Answer: Chicago has a fantastic rooftop bar scene, offering stunning skyline views along with creative cocktails—perfect for celebrating a 21st birthday. Since you have a quick weekend, it’s best to focus on rooftops that are centrally located near the Magnificent Mile, River North, or the Loop for convenience.

Answer: Arriving in Chicago around 4 PM on a Saturday gives you a tight window, but it is definitely possible to see both the Bean and Navy Pier without overexerting yourself, especially if you plan transportation carefully. Given your mobility considerations, minimizing walking is key.

Answer: For travelers looking for self-service laundry options in downtown Chicago, there are several hotels that offer laundry facilities or have nearby access to laundromats. While full-service hotels typically provide laundry services for a fee, some hotels do offer laundry rooms for guest use. Here are a few options to consider:

Answer: It’s great that you’re interested in exploring Chicago’s incredible architecture from the river! Chicago is famous for its architectural history, and a river cruise is one of the best ways to experience the city’s skyline and learn about its unique buildings. Since you mentioned you’re not fans of organized tours but are interested in narration, you’ll likely appreciate some of the more relaxed yet informative cruise options. Here are a few of the best architecture river cruises in Chicago, each offering a slightly different experience:

Answer: Your itinerary looks great! It's packed with fun activities without being overly rushed, and you've really planned for some key Chicago experiences. Below are some thoughts and additional suggestions for your trip:

Answer: If you're looking for a spot to grab a drink before a White Sox game near Guaranteed Rate Field, there are several great options within walking distance that offer a good pre-game atmosphere. Here are some of the top choices for fans looking to unwind before the game:

Answer: Hi there,

Answer: Finding a budget-friendly hotel near Lincoln Park in Chicago is definitely doable! The area is home to a mix of boutique hotels, chain options, and guesthouses that are within a short walking distance (or a 30-minute walk) from the Lincoln Park neighborhood. Here are some medium-priced hotel options that would fit your criteria:

Answer: It sounds like you're looking for some great, easy meal options for Christmas Eve and Christmas Day while staying near Northwestern Hospital in Chicago. Since many places are closed on Christmas Day, I’ll provide options that should work for both Christmas Eve and Christmas Day. Some of these places will offer takeout or pre-made meals, and others might provide options for you to heat up in your hotel room.

Answer: Sounds like you’ve got a fun girls' weekend ahead! Chicago is full of great things to see and do, even in the cold winter months. Here’s a breakdown of your questions to help you make the most of your trip:

Answer: It sounds like you're choosing between two great options in a fantastic location, and it really comes down to your priorities for your stay! Let me break down some key factors to help you decide between the Royal Sonesta and Intercontinental.

Answer: If you're looking for Italian or steakhouse options near Second City in Chicago, you're in luck! The area around Second City in Old Town is home to several great dining choices. Here are some top recommendations for both Italian and steakhouse cuisine:

Answer: Good questions — choosing between and depends a bit on what you value most: nightlife, easy access to transit, proximity to shopping/ restaurants, or hotel-amenities. Since you say price on Booking.com is about the same, here’s a breakdown of how they compare in terms of dining / restaurant and easy access to transportation and city amenities.

Overview of Each Hotel

Answer: It sounds like you're referring to a couples-only retreat that offers a romantic getaway with themed cottages, private pools, and hot tubs. While Sybaris is a well-known option in the Chicago area, there are a few other possibilities that may match what you're looking for, especially in the western suburbs or nearby areas.

Answer: It sounds like you're looking for a centrally located hotel in Chicago that offers great access to attractions, is comfortable for both of you, and fits within your budget of $300-$450 per night. With your preferences in mind, here are some great hotel options for your stay in Chicago in April or May:

Answer: If you're looking for restaurant deals or discounts in Chicago, there are several platforms and resources you can use to find great offers. Here are some of the best options for finding discounts on meals:

Answer: The Hampton Inn Downtown/North Loop/Michigan Ave is indeed in a very convenient location. It’s centrally situated and within walking distance to many major attractions, making it a great choice for sightseeing. The area around Michigan Avenue (including the North Loop) is a hub for tourists and locals alike, with plenty of things to do. You’ll be able to easily access public transportation, including the “L” (Chicago’s elevated train system), which is great for avoiding high Uber/Lyft costs, especially with younger children. You won’t need a car, which is ideal when traveling with kids, as there are many places to explore by foot.

Answer: When driving to Chicago from the Detroit suburbs and avoiding downtown driving, it's a great idea to stay in a suburb with easy access to public transportation or Lyft rides to the city. Here are some suburban options that will allow you to comfortably get to the Chicago Theater while being mindful of your husband's wheelchair accessibility needs:

Answer: Yes, Lake Michigan is visible from much of Lakeshore Drive, particularly in sections that run along the edge of the city near the lakefront. As you drive along the northern and southern stretches of Lakeshore Drive, you'll get multiple glimpses of the lake, especially as the road curves close to the shore. In some areas, such as the stretch near Lincoln Park or near the Museum Campus, the lake views are particularly scenic and open, offering nice vistas of the water.

Answer: For your early morning flight out of O'Hare, it's important to allow enough time to check in, get through security, and possibly deal with unexpected delays. Here's a breakdown of the key things to consider:

Answer: Chicago is a vibrant and exciting city, but like any major urban area, it’s important to approach safety with some awareness, especially when traveling solo. Based on your previous solo travel experience in New York, Toronto, Berlin, and Iceland, you’re likely already familiar with how to navigate a city and stay aware of your surroundings. That being said, here’s an honest breakdown to help you feel confident about your trip:

Answer: There isn't a direct Metra line from O'Hare to Ravenswood, but there are several options to consider based on your preferences for convenience and ease.

Answer: For your upcoming visit to Chicago in late August, it’s a good idea to plan ahead and book some activities in advance. Late August is a popular time to visit Chicago, especially with the summer festivals, so certain tours and attractions can sell out or fill up quickly. Here’s a breakdown of the activities you’re considering and whether it’s recommended to book in advance:

Answer: The weather in Chicago today is cold — around freezing (32 °F / 0 °C) with snow and flurries in parts, and likely cloudy or overcast through much of the day.

Answer: If you're looking for a reliable and high-quality limo service in Chicago for long-distance travel, there are several reputable companies you can consider, aside from the one you've used in the past. Here are some options, including both local companies with online booking capabilities and national chains that offer excellent services in Chicago:

Answer: Chicago offers a wealth of options for hosting a milestone birthday, especially if you’re looking for a combination of a shared bar, dance floor, and the possibility of live music or a DJ. Since you’re planning for a midweek evening and a relatively small group of about 10 people, you have flexibility to either book a semi-private space or a smaller venue that can feel intimate yet lively.

Answer: Chicago is famous for its iconic deep dish and stuffed pizzas, and it's understandable that you're looking for a place where you can enjoy both types of pizza fresh and hot! While many pizzerias specialize in one or the other, there are a few places that offer both deep dish and stuffed pizza options, and they’re known for making them fresh to order. Here are some of the best options for you:

Answer: When arriving at Union Station and looking to exit toward Adams Street near the Fifth Third Center (where you typically exit when heading to the station), it can be a bit tricky since there are multiple exits and pathways within the station. Here's a step-by-step guide to help you find your way out through the same spot you use when heading back to the station:

Answer: If you're looking for early breakfast options between Hi Chicago Hostel and the Riverwalk, there are several great spots nearby to get your day started. Whether you're looking for a quick bite or a sit-down meal, here are a few recommendations:

Answer: It's exciting that you're heading to Chicago in May! The city has a lot to offer in terms of sports, so you'll definitely find something to enjoy. Here's what you can expect during your stay from May 1st to May 4th:

Answer: Hi there,

Answer: Both Andy's and The Tortoise Club offer great food and live jazz in Chicago, but they each provide slightly different experiences. Here’s a breakdown of what you can expect from each to help you decide which is the better choice for your dinner and live music night:

Answer: Your two-night itinerary looks like an exciting mix of baseball, sightseeing, and good food, and you're hitting some great spots around Chicago! Let’s go through your plan and offer some feedback and suggestions to help you make the most of your short trip. I’ll also address your concerns about safety and transit options.

Answer: It sounds like you're planning a lovely stay in the northern suburbs of Chicago! Glenview, Evanston, Wilmette, and Glencoe are all great areas to explore, and they offer plenty of things to do without having to travel into downtown Chicago. Here's a breakdown of what you can enjoy in each of these areas:

Answer: It sounds like you’re planning a wonderful short stay in Chicago before your train trip on the California Zephyr! Here are some detailed answers to your questions:

Answer: Traveling from the Northwest suburbs into Chicago to visit Off Color Brewing and Guinness Taproom can be a smooth trip with some planning. Assuming you’re taking Metra from the NW suburbs, you’ll most likely arrive at Union Station or Ogilvie Transportation Center in downtown Chicago.