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Frequently Asked Questions

After landing at O’Hare, what’s the most straightforward way to reach the Payless rental counter from Terminal 5 versus Terminals 1–3?

Regardless of your arrival terminal at O'Hare, the process to reach the Payless counter is streamlined and well-signed. From Terminals 1, 2, and 3, follow the overhead signs for the Airport Transit System (ATS) or rental car shuttles, which will take you to the Multi-Modal Facility (MMF). If you arrive at the international Terminal 5, you will also follow signs for ground transportation to a designated shuttle bus pickup area. These complimentary shuttles run continuously, providing a direct and convenient connection to the rental car center where the Payless desk is located.

If I’m connecting through O’Hare with only a few hours, what timeline should I plan for picking up a Payless car and getting back to the terminals?

Picking up a rental car during a short connection at O'Hare requires careful time management. You should budget at least 20-30 minutes for the shuttle ride from your terminal to the Multi-Modal Facility and back. The pickup process itself can vary, so it's wise to allow another 30-45 minutes at the Payless counter, especially during peak travel times. Factoring in the time to return the vehicle and get back through security, a layover of several hours is necessary to make this a stress-free experience.

Where do rideshare drop-offs need to happen at ORD if I want to go straight to Payless without entering the terminal again?

If you are arriving at O'Hare via a rideshare service specifically to pick up your rental, the most efficient drop-off point is the Multi-Modal Facility (MMF). This facility houses the rental car counters, including Payless, and is directly accessible by car. Instruct your driver to follow the airport signs for 'Rental Car Return' or 'Multi-Modal Facility' rather than the terminal departures or arrivals lanes. This will place you right at the building where the rental counters are located, saving you a trip through the terminals.

What should I expect at Payless at ORD if my flight arrives during a snowstorm and roads around the airport are slow?

Arriving at O'Hare during a snowstorm means you should anticipate potential delays across all airport services. The rental car shuttles will still operate but may run on a slower schedule due to challenging road conditions. At the Payless counter, the staff will be managing the situation, but it's wise to be prepared for longer wait times as other travelers may also be delayed. Pack your patience, have your reservation information ready, and allow plenty of extra time for the entire pickup process, from baggage claim to driving away.

How do I plan a pickup at Payless if I’m traveling with skis, a stroller, or oversized luggage and need space to reorganize after baggage claim?

When traveling with bulky items, it's best to manage them in stages. After collecting your oversized luggage from baggage claim, you can use a luggage cart to transport everything to the rental car shuttle bus. Once you arrive at the Multi-Modal Facility and complete your rental paperwork at the Payless counter, you will proceed to the garage to pick up your vehicle. This garage area typically offers enough space to load your skis, stroller, and bags into the car without feeling rushed by terminal traffic.

What’s the best plan if my group lands on different flights and we want one person to pick up the Payless car while others wait at ORD?

A great strategy is to have the designated driver head directly to the Multi-Modal Facility via the airport shuttle to pick up the Payless rental car. While they handle the paperwork and vehicle retrieval, the rest of the group can wait comfortably in the arrivals area of their terminal. Once the driver has the car, they can coordinate via phone and drive to the terminal's passenger pickup curb to collect everyone and their luggage, which is often more efficient than having the whole group travel to the rental center.

If I’m staying in Rosemont tonight, what’s the easiest route from the Payless facility to hotels around the convention center area?

Driving from the O'Hare rental car facility to Rosemont hotels is a very short and straightforward trip. After exiting the rental car garage, follow the signs for Mannheim Road South. Most hotels in the Rosemont and convention center area are located just a few minutes down Mannheim Road or on adjacent streets like Higgins Road or River Road. Using a GPS is always helpful, but the proximity of Rosemont to the airport makes this one of the easiest post-pickup drives you can make.

What’s the least confusing way to drive from ORD to the Loop if I’m not used to multi-lane interchanges and frequent exits?

For a less stressful drive to the Loop, the key is to get onto the main expressway and stay there. From the rental facility, follow signs for I-190 East, which will seamlessly merge onto I-90 East, also known as the Kennedy Expressway. To avoid the stress of last-minute lane changes, it's best to stay in the center or center-left lanes for the majority of the drive. Use your preferred navigation app for guidance on which exit to take as you get closer to your downtown destination.

If my hotel is near Magnificent Mile, what’s a realistic plan for unloading luggage without getting stuck in traffic or bus-only zones?

Navigating to a hotel near the Magnificent Mile requires a bit of planning, especially for unloading. Before you arrive, check your hotel's website or call them to ask about their specific loading zone or valet entrance location, as it's often on a side street rather than Michigan Avenue itself. Plan to pull in, unload your luggage with the help of a bellhop if available, and then have one person proceed to the designated parking garage. Trying to park first or leaving the car unattended on the street is generally not a practical option in this busy area.

How should I handle driving into downtown Chicago if I’m arriving during a Cubs game, Bears game, or a major concert night?

If your arrival coincides with a major event, adjusting your route and timing is crucial. Check a real-time traffic app before leaving the Payless facility at O'Hare to see which expressways are most congested. Consider taking I-294 South to I-290 East (the Eisenhower Expressway) as an alternative to the Kennedy (I-90) if traffic is heavy near downtown. Most importantly, allow for significant extra travel time, as event traffic can cause gridlock on both highways and local streets.

What are the most common navigation mistakes visitors make leaving O’Hare, and how can I avoid missing the correct ramp right after pickup?

A common mistake when leaving O'Hare is not getting into the correct lane early enough for the major highway interchanges. The signs for I-90, I-294, and I-190 appear quickly after you exit the rental facility. To avoid missing your turn, program your destination into a GPS before you start driving and listen carefully to the lane guidance. It's also wise to have a passenger help navigate, as the initial series of ramps can be confusing for first-time visitors.

If I’m heading from ORD to Navy Pier, what should I know about road closures, one-way streets, or weekend congestion near the lakefront?

Driving to Navy Pier, especially on a weekend, means navigating through some of Chicago's busiest areas. The final approach involves city streets that can be congested, and Lake Shore Drive can experience closures for events. Be aware that many streets downtown are one-way, so relying on a GPS is essential. For a smoother experience, consider parking in a nearby garage like those at Grand or Illinois streets and walking the final few blocks to the pier to avoid the heaviest traffic right at the entrance.

What’s the simplest way to reach McCormick Place from ORD with a rental car if I’m arriving for a convention?

The most straightforward route from O'Hare to McCormick Place is to take I-190 East to I-90 East (Kennedy Expressway) toward downtown. Continue on I-90/94 through the city center and then follow signs for I-55 North toward Lake Shore Drive. McCormick Place has its own dedicated exit from I-55, which is clearly marked. This route keeps you on major expressways for most of the journey, minimizing complex turns on city streets until the very end of your trip.

If I’m visiting the Museum Campus (Field Museum, Shedd, Adler), what’s the best approach to parking and avoiding traffic backups at peak times?

To best enjoy the Museum Campus, plan to arrive early in the day, ideally before 10 a.m., to secure a spot in the main Soldier Field parking garage. This location provides central access to all three museums. Traffic on Lake Shore Drive and near the campus entrance can become very heavy, especially on weekends and during the summer. An alternative strategy is to park in a garage in the nearby South Loop neighborhood and enjoy a pleasant walk or a short rideshare to the museums, bypassing the worst of the congestion.

How difficult is it to drive from ORD to Wrigleyville, and what should I expect near the stadium on game days?

Driving from O'Hare to Wrigleyville is relatively simple on non-game days, typically involving taking the Kennedy Expressway (I-90) to the Addison Street exit. However, on game days, the area becomes extremely congested, and street parking is heavily restricted to residents. If your visit coincides with a Cubs game, it is highly advisable to park your rental car at your hotel or in a garage several blocks away from the stadium and then walk or use public transit for the final approach to avoid the gridlock.

If I’m staying in West Loop or Fulton Market, what’s the easiest way to get there from ORD without getting pulled into downtown gridlock?

To reach the West Loop or Fulton Market from O'Hare, you can avoid the most intense downtown traffic by taking a slightly different route. Follow I-190 East to I-90 East (Kennedy Expressway), but exit at Ogden Avenue or Lake Street before you reach the heart of the Loop. These exits will lead you directly into the West Loop area. This approach allows you to bypass the congested interchanges and dense traffic found further east, making for a much smoother arrival.

How should I plan a quick stop for groceries or supplies after picking up at Payless near ORD without detouring far off route?

After leaving the Payless facility at O'Hare, there are several convenient options for a quick stop. Many major grocery and big-box stores are located along Mannheim Road and Touhy Avenue, just a few minutes' drive from the airport. You can easily make a stop in nearby suburbs like Rosemont, Des Plaines, or Park Ridge before getting on the main expressways toward your final destination. A quick search on your phone's map app for 'grocery store' will show numerous choices right along your path.

If I’m basing in Schaumburg for a few days, what are the easiest drive times to avoid between ORD and the northwest suburbs?

The drive between O'Hare and Schaumburg can be subject to heavy rush hour traffic. To ensure a smooth trip, try to avoid traveling westbound on I-90 during the afternoon rush, typically from 3:30 p.m. to 6:30 p.m. Similarly, the eastbound commute toward the airport is busiest during the morning hours, from about 6:30 a.m. to 9:00 a.m. Planning your drives during midday or later in the evening will generally result in a much quicker and less stressful journey.

What’s the best strategy for driving to and parking near Millennium Park when I only have a few hours for sightseeing?

For a short visit to Millennium Park, the most efficient strategy is to use the underground Millennium Park Garage, which has entrances on Michigan Avenue and Columbus Drive. While it is a convenient option, it's also one of the most popular, so arriving earlier in the day is recommended. To save time, you can often pre-book a parking spot online through various apps, which can streamline your arrival. This allows you to park directly beneath the park and access all the main attractions on foot.

If I want to visit Chinatown and then head back toward the airport, what’s the easiest sequence to avoid stressful downtown turns?

A great plan is to drive to Chinatown first, as it's easily accessible from the Dan Ryan Expressway (I-90/94). Take the exit for Cermak Road and find parking in one of the main lots or garages near the Chinatown Gate. After your visit, you can get back on the expressway heading north/west toward O'Hare without having to navigate the complex grid of downtown streets. This sequence keeps you on major highways for the bulk of your travel, making the trip much more manageable.

How should I plan a day trip from Chicago to Milwaukee with a Payless rental, including where traffic tends to bottleneck?

A day trip to Milwaukee is a fantastic option, and the drive is mostly straightforward on I-94 West. To avoid the worst traffic, try to leave the Chicago area before 7 a.m. or after 9:30 a.m. on a weekday. The most significant bottleneck often occurs north of the city, around the junction with I-294 and through the northern suburbs. Once you are past this area, the drive typically opens up. The return trip can be slow in the late afternoon, so planning to leave Milwaukee either before 3 p.m. or after 6 p.m. is advisable.

What’s a smooth driving plan for a first-time visitor going from Chicago to Indiana Dunes for a beach day without getting lost on exit-heavy highways?

For an easy drive to Indiana Dunes National Park, the Chicago Skyway (I-90 East) is often the most direct route. While it is a toll road, it generally has less traffic than other options. Follow I-90 East into Indiana, where it becomes the Indiana Toll Road. From there, your GPS will guide you to the appropriate exit for the park entrance you wish to visit. This route minimizes complex interchanges and keeps you on a single main highway for most of the journey.

If I’m driving from Chicago to Ann Arbor or Detroit, what should I know about construction season and timing across state lines?

When driving east from Chicago toward Michigan, be prepared for construction, especially during the summer and fall months. The route primarily follows I-94 East, and it's common to encounter lane reductions or detours in both Indiana and Michigan. Before you leave, check the Departments of Transportation websites for both states for any major project alerts. Also, remember that you will lose an hour when you cross from the Central Time Zone into the Eastern Time Zone in Indiana, so factor that into your arrival plans.

What’s the most relaxed way to reach Wisconsin’s Lake Geneva area from ORD, especially on summer weekends?

For a more scenic and potentially less congested drive to Lake Geneva on a summer weekend, consider taking state highways instead of the main interstate. After a short drive on I-294 North from O'Hare, you can exit and take routes like US-12 West. This path will guide you through smaller towns and more rural landscapes, offering a pleasant alternative to the potential stop-and-go traffic on I-94. While it may take slightly longer, it's often a much more enjoyable and relaxed start to a weekend getaway.

If I’m planning a Chicago-to-Starved Rock day trip, what departure time helps avoid the worst traffic getting out of the city?

To get a head start on a day trip to Starved Rock State Park, aim to be on the road leaving the Chicago area by 7:30 a.m. at the latest, especially on a weekend. The primary route, I-55 South, can get very busy with outbound traffic. An early departure helps you clear the most congested suburban stretches before the peak morning rush builds. This ensures you spend more of your day enjoying the park's trails and less time sitting in traffic.

How do Chicago’s street-parking signs typically trip up visitors, and what should I watch for in neighborhoods like Lincoln Park or Lakeview?

Chicago's street parking signs can be confusing due to multiple restrictions listed on a single pole. Always read the entire sign from top to bottom. Look for permit-only parking hours, which are common in residential neighborhoods like Lincoln Park, and be mindful of street cleaning days, which will be posted with specific dates and times. Another common issue is rush hour tow-away zones on main streets, where parking is prohibited during morning and evening commutes, so double-check the times carefully.

What’s the most practical plan for visiting The Art Institute if I’m driving—where to park, and how to handle quick drop-offs?

The most practical approach for visiting The Art Institute is to park in one of the nearby underground garages, such as the Millennium Park Garage or the East Monroe Street Garage. These offer direct, convenient access without having to search for limited street parking. For a quick drop-off, the museum has a designated lane on its Modern Wing entrance on Monroe Street. This allows passengers to get out safely while the driver proceeds to a parking garage.

If my Airbnb is on a narrow residential street, what’s a good approach for curbside unloading without blocking traffic or missing a street-cleaning window?

When unloading at an Airbnb on a narrow street, efficiency is key. Before you arrive, check online for any posted street cleaning schedules for that block to avoid a ticket. Pull over as close to the curb as possible and turn on your hazard lights to signal that you are temporarily stopped. Unload all your luggage onto the sidewalk first, then immediately move your car to a legal parking spot before carrying your belongings inside. This minimizes the time you are blocking the lane of traffic.

What’s it like driving in Chicago during winter mornings—visibility, plowing, and lane markings—if I’m coming from a warm-weather state?

Driving in Chicago during a winter morning can be a new experience if you're from a warmer climate. After a snowfall, main roads are usually plowed, but lane markings may be obscured, requiring you to follow the flow of traffic carefully. Be prepared for reduced visibility from falling snow or spray from other vehicles, and give yourself significantly more braking distance. It's important to drive slower than you normally would and be extra cautious at intersections, which can remain icy even after plowing.

If I’m planning an early-morning departure from downtown to ORD, how much time should I allow for expressway slowdowns and terminal drop-off?

For an early-morning trip from downtown to O'Hare, it's wise to budget more time than you think you need. Even before the main rush hour, the Kennedy Expressway (I-90 West) can experience slowdowns starting as early as 5:30 a.m. A safe plan is to allow at least 60 to 90 minutes for the drive itself, plus additional time for returning your rental car and taking the shuttle to your terminal. This buffer accounts for unexpected traffic and ensures a low-stress start to your travel day.

What’s the easiest way to return a Payless car at ORD if I’m also dropping off passengers with lots of luggage?

The most convenient method is to first drop off your passengers and their luggage at the departures curb of your airline's terminal. This allows them to proceed to check-in while you handle the car return. After the drop-off, you can follow the airport signs for 'Rental Car Return' to the Multi-Modal Facility. From there, you can take the quick and free airport shuttle back to the terminal to rejoin your party and go through security.

If I’m running late for a flight, what’s the most direct return approach at the Payless facility so I don’t miss the entrance or loop the airport roads?

When you're short on time, focus on the airport signage for 'Rental Car Return' as you approach O'Hare. These signs are large, clear, and will guide you directly to the entrance of the Multi-Modal Facility where Payless is located. Avoid following signs for 'Arrivals' or 'Departures,' as this can lead you into the terminal traffic loops. Following the specific rental return signs is the most foolproof way to get to the correct destination without any confusing detours.

What should I do if I realize I left something in the Payless rental car after I’m already back inside O’Hare?

If you realize you've left an item behind, the first step is to contact the Payless rental location at O'Hare directly. Have your rental agreement number and vehicle information handy to help them identify the car quickly. The staff can advise you on their lost and found procedure and whether the item has been located. Acting quickly provides the best chance of recovering your belongings before the vehicle is cleaned and rented to another customer.

If I get an alert light or a tire issue while driving around Chicago, what steps should I take before continuing my trip?

If a warning light appears on the dashboard or you suspect a tire issue, your safety is the top priority. Pull over to a safe location like a parking lot or a well-lit side street as soon as it is safe to do so. Consult the vehicle's owner's manual to understand what the light indicates. You should then contact the roadside assistance number provided by Payless with your rental agreement to receive instructions on how to proceed.

What kind of car setup works best for a Chicago trip with two adults and three kids, especially with winter coats and bulky bags?

For a family of five visiting Chicago, particularly in the winter, a minivan or a mid-size to full-size SUV is an excellent choice. These vehicle types offer the necessary passenger space to ensure everyone is comfortable, even while wearing bulky coats. Crucially, they also provide ample cargo room in the back for luggage, strollers, and shopping bags. Opting for a larger vehicle from the Payless fleet will make your family's travels around the city much more pleasant and less cramped.

How should I plan my routes if I want to drive the Chicago lakefront area but avoid roads that frequently become stop-and-go?

To enjoy a drive along the lakefront, timing is everything. Lake Shore Drive (now Jean-Baptiste Pointe DuSable Lake Shore Drive) offers stunning views but can be very congested during weekday rush hours and on sunny summer weekends. For a more relaxed experience, plan your drive for a weekday during the late morning or early afternoon. Alternatively, an early weekend morning drive can be beautiful and quiet, allowing you to take in the skyline and lake views without the stress of heavy traffic.

If I’m visiting friends in Hyde Park, what’s the easiest driving approach from ORD that avoids complicated downtown navigation?

A great route from O'Hare to Hyde Park that bypasses most of the downtown congestion is to use the expressway system strategically. Take I-294 South from the airport to I-290 East. Then, merge onto I-90/94 East (the Dan Ryan Expressway) and follow it south past the downtown area. You can then exit at Garfield Boulevard and take local streets east toward Hyde Park. This route keeps you on major highways and avoids the dense traffic of the Loop.

If I’m planning to visit multiple neighborhoods in one day (Logan Square, Wicker Park, Pilsen), what’s the best way to sequence driving and parking?

A smart way to explore multiple neighborhoods is to group them geographically and use a 'park once' strategy. For example, you could drive to the Wicker Park/Bucktown area and find a spot in a public garage or a non-permit street space. From there, you can explore both neighborhoods on foot. Afterward, drive south to Pilsen, which is a distinct trip, and find parking there to explore its murals and restaurants. This approach is more efficient than trying to drive and repark every few blocks within a single area.

What’s a practical plan for returning the Payless car and still having time to eat or shop in the terminal before a flight out of ORD?

To ensure a relaxed end to your trip, plan to return your Payless vehicle at least three hours before a domestic flight or four hours before an international one. The return process at the Multi-Modal Facility is typically quick, but you must account for the shuttle ride back to your terminal. This generous time buffer allows you to check your bags, clear security without rushing, and still have plenty of time to enjoy a meal or browse the shops near your departure gate.

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